JP2006169174A - Method for producing difluoromethyl ether derivative - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for readily and efficiently producing a difluoromethyl ether derivative useful as a liquid crystal material. <P>SOLUTION: The method for producing the difluoromethyl ether derivative involves reacting a compound represented by formula (1) (wherein, ring group A and ring group B are each independently a carbon ring group which may include a hetero atom as an atom constituting the ring, and in which the hydrogen atom may be substituted with a halogen atom; R<SP>a</SP>is a monovalent organic group; R<SP>b</SP>is a monovalent organic group, a hydrogen atom, a halogen atom (b), a cyano group or -SF<SB>5</SB>; and M is a hydrogen atom or an alkali metal atom) with a fluorination agent to convert both of -COOM parts in the compound (1) to fluorine atoms. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a simple and efficient method for producing a difluoromethyl ether derivative useful as a liquid crystal material.

  Liquid crystal display devices are used as display devices for various devices such as office automation equipment, measuring instruments, automobile meters, home appliances, watches, and calculators. In recent years, liquid crystal display devices have been required to be further reduced in size, reduced in power consumption, and faster in response, and thus liquid crystals having a low threshold voltage and a low viscosity are required.

It is known that the threshold voltage (V _th ) of a liquid crystal element is obtained by the following formula (1).
V _th = π (K / ε ₀ Δε) / 2 (1)
(Where K is the elastic constant of the liquid crystal in the device, ε ₀ is the dielectric constant of the liquid crystal in vacuum, and Δε is the value of dielectric anisotropy).
From the above equation (1), in order to reduce _Vth , the Δε value may be increased or the K value may be decreased. However, since adjustment of the K value is very difficult, it is necessary to lower _Vth by using a liquid crystal having a large Δε value. In addition, a low-viscosity liquid crystal is required for high-speed response. In order to prepare such a liquid crystal, a liquid crystalline compound having a large Δε value and a low viscosity is required.

As a liquid crystalline compound having a large Δε value and low viscosity, the following formula (A) (see Patent Document 1), the following formula (B) (see Patent Document 2), and the following formula (C) (see Patent Document 3): A compound having a —CF ₂ O— structure, such as a compound represented by the formula, has been proposed, and various methods for its production have been proposed (see, for example, Patent Document 2, Patent Document 4, and Patent Document). 5 and Patent Document 6).

JP-A-5-112778 German Patent Application Publication No. 195311165 International Publication No. 96/11897 Pamphlet JP-A-5-255165 JP 2000-95715 A JP 2003-261478 A

  However, the above production method is a multi-stage reaction, requires ultra-low temperature conditions of about −60 to −70 ° C., requires a complicated purification operation because a by-product is generated, has a low yield, etc. There was a problem.

  The present invention has been made to solve the above-described problems, and provides a simple and efficient method for producing a difluoromethyl ether derivative useful as a liquid crystal material. That is, the present invention provides the following inventions.

<1> A compound represented by the following formula (1) and a fluorinating agent are reacted to convert both of the —COOM moieties in the compound (1) into fluorine atoms. The manufacturing method of the compound represented by these. However, the symbols in the formulas have the following meanings.
Ring group A and ring group B: each independently represents a carbocyclic group which may contain a hetero atom as an atom constituting the ring, and a hydrogen atom in the group may be substituted with a halogen atom.
R ^a : a monovalent organic group.
R ^b : a monovalent organic group, a hydrogen atom, a halogen atom (b), a cyano group, or —SF ₅ .
M: a hydrogen atom or an alkali metal atom.

<2> The cyclic group A and the cyclic group B are each independently a 1,4-phenylene group (one or two hydrogen atoms in the group may be substituted with a fluorine atom) or trans-1 The manufacturing method as described in <1> which is a 4-cyclohexylene group.
<3> The production method according to <1> or <2>, wherein the fluorinating agent is xenon difluoride or fluorine gas.

  According to the present invention, a difluoromethyl ether derivative useful as a liquid crystal material can be easily and efficiently produced.

  In the present specification, the compound represented by the formula (1) is also referred to as the compound (1). The same applies to other compounds.

In the aliphatic hydrocarbon groups (a) to (f) in the present invention, some or all of the hydrogen atoms in the groups may be substituted with halogen atoms. As the halogen atom to be substituted, a chlorine atom or a fluorine atom is preferable, and a fluorine atom is particularly preferable. In addition, these aliphatic hydrocarbon groups may have an etheric oxygen atom between carbon-carbon atoms, and when these aliphatic hydrocarbon groups are bonded to a cyclic group, It may have an etheric oxygen atom at the bond terminal with the group.
As the halogen atoms (a) to (f) in the present invention, a chlorine atom or a fluorine atom is preferable, and a fluorine atom is particularly preferable.

  In the present invention, the ring group A and the ring group B each independently represent a carbocyclic group that may contain a hetero atom as an atom constituting the ring. The carbocyclic group which may contain a hetero atom as a ring-constituting atom is a 6-membered cyclic group consisting of a carbon atom and a hydrogen atom as a ring-constituting atom, or as an atom constituting a ring. It is a 6-membered ring group consisting of a hetero atom, a carbon atom and a hydrogen atom. As a hetero atom, an oxygen atom or a sulfur atom is preferable. The number of heteroatoms constituting the ring may be plural, and is preferably one or two. When two or more heteroatoms are present, the heteroatoms are not adjacent. Moreover, these 6-membered ring groups may contain an unsaturated bond.

These ring groups have bonds at the 1-position and 4-position. In this specification, the right side of the cyclic group is the 1st position and the left side is the 4th position (for example, in the cyclic group A in the compound (2), the position bonded to the carbon atom of —CF ₂ O— 1st position, and the position bonded to the oxygen atom of —CF ₂ O— in the ring group B is position 4. ^Ra is bonded to the 4th position of the ring group A, and R position is bonded to the 1st position of the ring group B. ^b is bonded. The same applies to other ring groups hereinafter.) When the ring group is a 1,4-cyclohexylene group, the bond at the 1-position and 4-position is at the trans position.

  The hydrogen atom bonded to the carbon atom constituting the ring group A and the ring group B may be substituted with a halogen atom (a). When the cyclic group A or the cyclic group B is a 1,4-phenylene group, the number of halogen atoms (a) to be substituted is 1 to 4, and preferably 1 or 2. The bonding position of the halogen atom (a) is preferably the 2-position and / or the 6-position. When the cyclic group A or the cyclic group B is a trans-1,4-cyclohexylene group, the number of halogen atoms (a) to be substituted is 1 to 4. When a plurality of halogen atoms (a) are substituted, each halogen atom (a) is preferably bonded to a different carbon atom. The halogen atom (a) may be bonded to the carbon atom at the 1-position or 4-position of the cyclohexylene group (particularly the 1-position of the ring group B and the 4-position of the ring group A).

  Specific examples of the ring group A and the ring group B are shown below. In this specific example, the 1,4-phenylene group is represented by “Ph” and the trans-1,4-cyclohexylene group is represented by “Cy”. In addition, a substituent bonded to the 2nd and 6th positions of the cyclic group is attached to the right side of the symbol representing the cyclic group, and a substituent bonded to the 3rd and 5th positions is labeled on the left side of the symbol representing the cyclic group. Along with it. The position of the oxygen atom or sulfur atom in the 6-membered ring in which the carbon atom constituting the ring of the trans-1,4-cyclohexylene group is substituted with an oxygen atom or a sulfur atom is also treated and expressed in the same manner as the substituent.

  Among the following specific examples, the cyclic group A and the cyclic group B include a 1,4-phenylene group (3), a trans-1,4-cyclohexylene group (11), and a 2-fluoro-1,4-phenylene group. (4) or 2,6-difluoro-1,4-phenylene group (7) is preferred.

R ^a represents a monovalent organic group. R ^a is a group containing one or two 6-membered ring groups having a bond at the 1-position and 4-position, similar to the ring group A and the ring group B, or includes a ring group Preferably no group. When R ^a is the former group, the aliphatic hydrocarbon group (a) is bonded to the 4-position of the 6-membered cyclic group present at the terminal (the position farthest from the cyclic group A) in R ^a . It is preferable. Two or three 6-membered ring groups including the ring group A may be directly bonded (bonded by a single bond) or may be bonded via a linking group. When R ^a is a group not containing ^a cyclic group, R ^a is preferably an aliphatic hydrocarbon group (b).

R ^a is preferably a group represented by the following formula (3).

  The ring group C and the ring group D each independently represent a carbocyclic group that may contain a hetero atom as an atom constituting the ring. The cyclic group C and the cyclic group D are the same groups as the cyclic group A and the cyclic group B described above, and preferred embodiments are also the same.

Z ¹ and Z ² each independently represents a single bond or a divalent linking group. The linking group is preferably a linking group consisting of 2 to 4 atoms and having no side chain. The linking group is preferably a linking group consisting of 2 to 4 carbon atoms, or a linking group consisting of 1 to 3 carbon atoms and one oxygen atom, and a linking group consisting of 2 carbon atoms. Or a linking group consisting of one carbon atom and one oxygen atom is particularly preferred.
The atom bonded to the carbon atom in the linking group is preferably a hydrogen atom and / or a fluorine atom. When two or more carbon atoms are present adjacent to each other in the linking group, the bond between the carbon and carbon atoms may be a single bond or an unsaturated bond.

Z ¹ and Z ² are each a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —CH ₂ O—, —OCH ₂ —, —CF ₂ CF ₂ —, — (CF _{2). ) 4 -, - CF = CF} -, - CF 2 O-, or -OCF ₂ -, more preferably a single _{bond, -CF 2 CF 2 -, -} CF = CF -, - CF 2 O-, or -OCF ₂ -Is particularly preferable, and a single bond is particularly preferable from the viewpoint of the reactivity of the compound (1).
p and q each independently represents 0 or 1. R ¹ represents an aliphatic hydrocarbon group (c) described later.

R ^b represents a monovalent organic group, a hydrogen atom, a halogen atom (b), a cyano group, or —SF ₅ . When R ^b is a monovalent organic group, R ^b is a group containing one 1,4-phenylene group similar to the cyclic groups A to D therein, or an aliphatic hydrocarbon group (d ) Is preferable. When R ^b is the former group, an aliphatic hydrocarbon group (e), a halogen atom (c), or a cyano group is bonded to the terminal (1-position side) of the 1,4-phenylene group. Is preferred. The ring group B and the 1,4-phenylene group may be directly bonded (bonded by a single bond) or may be bonded via a linking group.

R ^b is preferably a monovalent organic group containing a group represented by the following formula (4) at the end (wherein X ¹ and X ² are each independently a hydrogen atom or a halogen atom (d)). R ² represents an aliphatic hydrocarbon group (f) or the like described later). The 1,4-phenylene group in the following formula (4) is preferably a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, or a 2,6-difluoro-1,4-phenylene group.

In the compounds (1) and (2), the terminal structure on the ring group B side (the structure bonded to the 1-position of the ring group B) is preferably a structure represented by the formula (4). In addition, the ring group B to which R ^b is bonded can also have a structure represented by the formula (4). Therefore, when R ^b does not include the structure represented by the formula (4), the ring group B to which R ^b is bonded is a structure represented by the formula (4), and R ^b represents the formula (4). ), The cyclic group B is preferably a 6-membered cyclic group similar to the cyclic groups A to D that are not limited to 1,4-phenylene groups.

  The following compound (1a) is preferable as the compound (1) in the present invention, and the following compound (2a) is preferable as the compound (2).

In the compound (1a) and the compound (2a), the cyclic group A, the cyclic group C, and the cyclic group D have the same meaning as described above. The ring group B ¹ represents a carbocyclic group which may contain a hetero atom as an atom constituting the ring, and is the same group as the ring groups A to D, and the preferred embodiment is also the same.
Z ¹ and Z ² have the same meaning as described above, and Z ³ is a single bond or a divalent linking group. The divalent linking group is the same group as the linking group in Z ¹ and Z ² , and the preferred embodiment is also the same. Z ³ is preferably a single bond. X ¹ and X ² have the same meaning as described above.
p, q, and r each independently represents 0 or 1. p + q + r is preferably an integer of 0 to 2, particularly preferably 1. Furthermore, p or q is 1 and r is 0 from the viewpoint of the reactivity of the compound (1), the solubility in the reaction solvent, and the ease of isolation and purification of the compound (2). preferable.

R ¹ represents a monovalent aliphatic hydrocarbon group (c), a hydrogen atom, or a halogen atom (e).
When R ¹ is a monovalent aliphatic hydrocarbon group (c), the aliphatic hydrocarbon group (c) may have a branched structure, may have an asymmetric carbon atom, You may have a structure containing an unsaturated bond. Examples of the structure containing an unsaturated bond include —CH═CH—, —CF═CF—, —CH═CF—, and —CF═CH—.

R ¹ is preferably a monovalent aliphatic hydrocarbon group (c). Examples of the aliphatic hydrocarbon group (c) include an alkyl group, an alkenyl group, an alkoxy group, an alkoxyalkyl group, a polyfluoroalkyl group, a polyfluoroalkenyl group, a perfluoroalkyl group, and a perfluoroalkoxy group. Further, these monovalent aliphatic hydrocarbon groups (c) preferably have 1 to 8 carbon atoms (note that the number of carbon atoms in the alkoxyalkyl group refers to the number of carbon atoms in the alkyl group portion and the alkoxy group portion to be substituted therewith). Refers to the total number of carbons).

  Specifically, a linear alkyl group having 1 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a linear alkoxyalkyl group having 2 to 6 carbon atoms, a linear alkenyl group having 2 to 8 carbon atoms, Alternatively, a linear polyfluoroalkenyl group having 2 to 8 carbon atoms is preferable, and the following groups are particularly preferable.

_{- (CH 2) k1 H (} k1 is an integer of 1 to _{8), - O (CH 2)} k2 H (k2 is an integer of 1 to _{8), - CH 2 O (CH} 2) k3 H (k3 is 1 4 _{integer), - (CH 2) 2} O (CH 2) k4 H (k4 is an integer of 1 to _{3), - (CH 2) 3} O (CH 2) k5 H (k5 is an integer of 1 to 3) _{, -CH = CH 2, -CH =} CHCH 3, -CH 2 CH = CH 2, -CH = CHCH 2 CH 3, -CH 2 CH 2 CH = CH 2, -CH = CHCH 2 CH 2 CH 3, - _{CH 2 CH 2 CH = CHCH 3} , -CH = CHF, -CH = CF 2, -CF = CF 2, -CH 2 CH 2 CH = CF 2, -CH 2 CH = CF 2, -CH 2 CH 2 CH ₂ CH═CF ₂ .

R ² represents a monovalent aliphatic hydrocarbon group (f), a hydrogen atom, a halogen atom (f), a cyano group, or —SF ₅ . When R ² is a monovalent aliphatic hydrocarbon group (f), the aliphatic hydrocarbon group (f) is the same group as the aliphatic hydrocarbon group (c).

  Examples of the aliphatic hydrocarbon group (f) include an alkyl group, an alkenyl group, an alkoxy group, an alkoxyalkyl group, a polyfluoroalkyl group, a polychloroalkyl group, and a polyfluoroalkoxy group. These groups preferably have 1 to 10 carbon atoms, and the following groups are particularly preferable.

_{- (CH 2) m1 H (} m1 is an integer of from 1 to _{10), - O (CH 2)} m2 H (m2 is an integer of 1 to _{8), - CH 2 O (CH} 2) m3 H (m3 is 1 4 _{integer), - (CH 2) 2} O (CH 2) m4 H (m4 is an integer of 1 to _{3), - (CH 2) 3} O (CH 2) m5 H (m5 is an integer of 1 to 3) _{, -CH = CH 2, -CH =} CHCH 3, -CH 2 CH = CH 2, -CH = CHCH 2 CH 3, -CH 2 CH 2 CH = CH 2, -CH = CHCH 2 CH 2 CH 3, - _{CH 2 CH 2 CH = CHCH 3} , -CF 3, -CHF 2, -CClF 2, -CH 2 CF 3, - (CH 2) m6 F ( although, m6 is 2-5 integer), - (CH _{2 ) 3 Cl, -OCF 3, -OCHF} 2, -OCClF 2, -O (CF 2) m7 F (m7 is 2 or _{3), - OCF 2 CHF 2} , -OCF 2 CHFCF 3, -CH 2 OCF 3, -CH = CHF, -CH = CF 2, -CF = CF 2, -CH 2 CH 2 CH _{= CF 2, -CH 2 CH =} CF 2, -CH 2 CH 2 CH 2 CH = CF 2.

R ² is preferably a perfluoroalkyl group having 1 to 3 carbon atoms, a perfluoroalkoxy group having 1 to 3 carbon atoms, a fluorine atom, a chlorine atom, a cyano group, or —SF ₅ , and a trifluoromethyl group or a trifluoromethoxy group. A fluorine atom or a cyano group is particularly preferable.

  M represents a hydrogen atom or an alkali metal atom. M is preferably a hydrogen atom, a lithium atom, a sodium atom, or a potassium atom from the viewpoint of reactivity with the fluorinating agent.

As the compound (1) in the present invention, a —CF ₂ O— structure in a specific example of the compound (2) described later is a structure represented by the following formula (8) (where M in the formula has the same meaning as described above). The compounds substituted in the above are preferred.

Compound (1) in the present invention can be produced by applying a known method to a known compound. Known methods include those described in “Organic Synthesis, coll. Vol”. II, 288p (1966), Japanese Patent Application Laid-Open No. 55-154936, European Patent Application Publication No. 1182190, and the like can be used.
For example, the compound (1) in the case where the cyclic group A is a 1,4-phenylene group has the following route (where R ^a and R ^b have the same meaning as described above. R ^c is a hydrogen atom, a lower alkyl group, Or Q ¹ represents a halogen atom, preferably a chlorine atom, a bromine atom and an iodine atom, and particularly preferably a bromine atom.

  That is, a phenylacetic acid derivative (21) and a succinic acid derivative (such as diethyl succinate) are reacted to obtain the following compound (22) (step 1). The compound (22) is halogenated to obtain the compound (23) (step 2). Next, the compound (23) and the compound (24) are reacted in an aprotic solvent (toluene, tetrahydrofuran, t-butyl methyl ether, dimethylformamide, sulfolane, methyl ethyl ketone, etc.) in the presence of a base such as potassium carbonate. Thus, compound (25) is obtained (step 3), and then compound (26) is obtained by hydrolysis reaction of compound (25) or the like (step 4). In addition, a compound (26) is a compound (1) in case the cyclic group A is a 1, 4- phenylene group.

The compound (1) in the case where the cyclic group A is a trans-1,4-cyclohexylene group can be produced, for example, according to the following route (provided that R ^a and R ^b represent the same meaning as described above, R ^d represents a hydrogen atom) Q ² represents a halogen atom, preferably a chlorine atom, a bromine atom or an iodine atom, and particularly preferably a bromine atom.
A cyclohexanone derivative (27) and a malonic acid derivative (such as diethyl malonate) are reacted to obtain the following compound (28) (step 5). Next, the compound (28) is hydrogenated and then halogenated to obtain the compound (29) (step 6). Further, the compound (29) and the compound (24) are reacted in an aprotic solvent (toluene, tetrahydrofuran, t-butyl methyl ether, dimethylformamide, sulfolane, methyl ethyl ketone, etc.) in the presence of a base such as potassium carbonate. Compound (30) is obtained (Step 7), and the compound (30) is subjected to a hydrolysis reaction or the like to obtain Compound (31) (Step 8). Compound (31) is compound (1) when ring group A is a trans-1,4-cyclohexylene group.

  The production method of the present invention is a method for obtaining compound (2) by reacting compound (1) with a fluorinating agent and substituting both of the two —COOM moieties in compound (1) with fluorine atoms. . As the fluorinating agent, xenon difluoride or fluorine gas is preferable.

  When xenon difluoride is used as the fluorinating agent, the fluorination reaction can be carried out with reference to literature (J. Org. Chem., (1983), 48, p. 4158-4159, etc.). For example, the compound (1) is dissolved in an aprotic solvent (methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,2-trichloro-1,2,2-trifluoroethane, etc.) Fluorination reaction is performed by introducing xenon difluoride into this solution. The amount of the aprotic solvent is preferably 0.5 to 100 mL with respect to 1 g of the compound (1). The amount of xenon difluoride is preferably 1 to 10-fold mol, particularly preferably 1 to 1.5-fold mol based on compound (1).

It is preferable to blow hydrogen fluoride into the reaction solution as necessary. In this case, the amount of hydrogen fluoride is preferably 0.5 to 100-fold mol and particularly preferably 1 to 10-fold mol based on compound (1). The reaction temperature is preferably 0 to + 100 ° C, particularly preferably 0 to + 50 ° C. The reaction time is preferably 1 to 120 hours. The reaction pressure is preferably atmospheric pressure or pressurization, and atmospheric pressure is particularly preferred.
After completion of the reaction, it is preferable to treat with an aqueous solution of an inorganic base such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide. After the treatment with a base, it is preferable to isolate the compound (2) by performing extraction and concentration with an organic solvent. Furthermore, the compound (2) is preferably subjected to purification treatment by distillation, recrystallization, sublimation, chromatography or the like.

When fluorine gas is used as the fluorinating agent, it can be carried out according to the literature (J. Org. Chem., (1969) 34, p. 2246-2450, etc.).
The fluorine gas can be used without being diluted, but it is usually preferable to use it diluted with an inert gas such as nitrogen or helium. In this case, the concentration of the fluorine gas is 1% by volume or more, and preferably 2 to 50% by volume. The supply flow rate of the fluorine gas is not particularly limited, and usually 5 to 1000 mL / min is preferable.
The reaction temperature is preferably −50 to + 100 ° C., particularly preferably −20 to + 50 ° C. The reaction time is preferably 1 to 120 hours. The reaction pressure is preferably atmospheric pressure or pressurization, and atmospheric pressure is particularly preferred.

As the solvent, common solvents such as water, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, trichlorofluoromethane, 1,1,2-trichloro-1,2,2-trifluoroethane, and the like can be used. Can be used. These solvents may be used alone or as a mixed solvent in which two or more solvents are mixed in an arbitrary ratio.
Further, in order to prevent hydrogen fluoride produced as a by-product during the fluorination reaction from affecting the reaction product, the fluorination reaction is preferably performed in the presence of a deoxidizing agent. Examples of deoxidizers include alkali metal fluorides such as sodium fluoride, potassium fluoride, and cesium fluoride; metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; calcium oxide, oxidation Examples thereof include metal oxides such as magnesium; amines such as triethylamine; ammonium salts such as tetrabutylammonium fluoride. The amount of the deoxidizer is preferably 50 to 1000% by mass with respect to the compound (1).
After completion of the fluorination reaction, it is preferable to perform post-treatment, isolation, and purification treatment in the same manner as in the case of carrying out the fluorination reaction with xenon difluoride.

As the compound (2) obtained by the production method of the present invention, the following compounds (2a-1) to (2a-10) are preferable. However, X < ³ >, X < ⁴ > and Y in a formula show a hydrogen atom, a chlorine atom, or a fluorine atom each independently, and it is preferable that they are a hydrogen atom or a fluorine atom.

As the compound (2a-1), the following compounds are preferred (in addition, the notation of a 6-membered cyclic group follows the above rules, and the alkyl group in the formula has a linear structure. The same applies hereinafter).
_{C 3 H 7 -Ph-CF 2} O-Ph-F
_{C 5 H 11 -Ph-CF 2} O-Ph F -F
_{C 3 H 7 -Ph-CF 2} O-Ph FF -F
^{_{C 3 H 7 -Ph F -CF 2}} O-Ph-F
^{_{C 5 H 11 -Ph F -CF 2}} O-Ph F -F
^{_{C 3 H 7 -Ph F -CF 2}} O-Ph FF -F
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph-F
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph F -F
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph FF -F
^{_{C 3 H 7 -Ph FF -CF 2}} O- F Ph-Cl
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph F -Cl
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph F -CN
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph FF -CN
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph F -CF 3
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph FF -CF 3.

^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph F -OCF 3
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph FF -OCF 3
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph F -SF 5
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph FF -SF 5
^{_{C 2 H 5 O-Ph FF}} -CF 2 O-Ph F -F
^{_{CH 3 OCH 2 -Ph FF -CF 2}} O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Ph FF -CF 2 O-Ph F -F
^{_{CFH 2 CH 2 CH 2 -Ph FF}} -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Ph} FF -CF 2 O-Ph FF -F.

As the compound (2a-2), the following compounds are preferable.
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph-F
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph F -F
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O- F Ph-Cl
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph F -Cl
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph F -CN
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph FF -CN
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph F -CF 3
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph FF -CF 3
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph F -OCF 3
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph FF -OCF 3
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph F -SF 5
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Ph-CF 2} O-Ph FF -F
^{_{C 2 H 5 -Cy-Ph F}} -CF 2 O-Ph FF -F
^{_{CH 3 -Cy-Ph FF -CF 2}} O-Ph FF -F
^{_{C 2 H 5 -Cy-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Cy-Ph FF}} -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Cy-Ph FF -CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Cy-}} Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Ph FF -CF 2 O-Ph FF -F.

_{^{C 2 H 5 -Cy O -Ph FF}} -CF 2 O-Ph FF -F
_{^{C 3 H 7 -Cy OO -Ph FF}} -CF 2 O-Ph FF -F
_{^{C 4 H 9 -Cy S -Ph FF}} -CF 2 O-Ph FF -F
_{^{C 5 H 11 -Cy SS -Ph FF}} -CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph-F
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph FF -CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-CH 2 CH 2} -Ph-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy- (CH 2} ) 4 -Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Cy-OCH 2 -Ph FF}} -CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 3 H 7 -Cy- (CH 2} ) 4 -Ph FF -CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy-CH 2}} O-Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Cy-OCF 2}} -Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -CF 2 CF 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy- (CF 2) 4 -Ph FF -CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F.

^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph-F
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph F -F
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O- F Ph-Cl
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph F -Cl
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph F -CN
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph FF -CN
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph F -CF 3
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph FF -CF 3
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph F -OCF 3
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph FF -OCF 3
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph F -SF 5
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph FF -SF 5.

_{CH 3 -Ph-Ph-CF 2} O-Ph FF -F
^{_{C 2 H 5 -Ph-Ph F}} -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Ph-Ph-}} CF 2 O-Ph FF -F ··· (2a-2)
^{_{CH 3 -Ph-Ph FF -CF 2}} O-Ph FF -F
^{_{C 2 H 5 -Ph-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 4 H 9 -Ph-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Ph-Ph FF}} -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} -Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Ph-Ph FF -CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Ph-}} Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Ph} -Ph FF -CF 2 O-Ph FF -F.

_{C 3 H 7 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph-F
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -F
_{C 3 H 7 -Ph-CH 2} CH 2 -Ph FF -CF 2 O- F Ph-Cl
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -Cl
_{C 3 H 7 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -CN
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -CN
_{C 3 H 7 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -CF 3
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph F -SF 5
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Ph-CH 2 CH 2} -Ph-CF 2 O-Ph FF -F
_{C 2 H 5 -Ph- (CH 2} ) 4 -Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Ph-OCH 2 -Ph FF}} -CF 2 O-Ph FF -F
_{C 2 H 5 -Ph-CH 2} CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 3 H 7 -Ph- (CH 2} ) 4 -Ph FF -CF 2 O-Ph FF -F
^{_{C 4 H 9 -Ph-CH 2}} O-Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Ph-OCF 2}} -Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} -CF 2 CF 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Ph- (CF 2) 4 -Ph FF -CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F.

^{_{CH 3 -Ph F -Ph-CF 2}} O-Ph FF -F
^{_{C 2 H 5 -Ph FF -Ph F}} -CF 2 O-Ph FF -F
CH ₃ ^-F Ph ^FF -Ph ^FF -CF ₂ O-Ph ^FF -F
C ₂ H ₅ ^-F Ph-Ph ^FF -CF ₂ O-Ph ^FF -F
^{_{C 3 H 7 -Ph F -Ph FF}} -CF 2 O-Ph FF -F
C ₄ H ₉ ^-F Ph ^F -Ph ^FF -CF ₂ O-Ph ^FF -F
^{_{C 5 H 11 -Ph FF -Ph FF}} -CF 2 O-Ph FF -F
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 - FF Ph F}} -Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} F -CF 2 CF 2 -Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 -CH = CHCH 2 CH 2}} -Ph FF -Ph FF -CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Ph-}} Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -} FF Ph-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F.

As the compound (2a-3), the following compounds are preferable.
^{_{C 3 H 7 -Cy-Cy-}} Ph FF -CF 2 O-Ph-F
^{_{C 5 H 11 -Cy-Cy-}} Ph FF -CF 2 O-Ph F -F
_{^{C 3 H 7 -Cy-Cy-}} Ph FF -CF 2 O- F Ph-Cl
_{^{C 5 H 11 -Cy-Cy-}} Ph FF -CF 2 O-Ph F -Cl
_{^{C 3 H 7 -Cy-Cy-}} Ph FF -CF 2 O-Ph F -CN
_{^{C 5 H 11 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -CN
_{^{C 3 H 7 -Cy-Cy-}} Ph FF -CF 2 O-Ph F -CF 3
_{^{C 5 H 11 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -CF 3
_{^{C 3 H 7 -Cy-Cy-}} Ph FF -CF 2 O-Ph F -OCF 3
_{^{C 5 H 11 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -OCF 3
_{^{C 3 H 7 -Cy-Cy-}} Ph FF -CF 2 O-Ph F -SF 5
_{^{C 5 H 11 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Cy-Ph-} CF 2 O-Ph FF -F
^{_{C 2 H 5 -Cy-Cy-}} Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Cy-Cy-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 2 H 5 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 5 H 11 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Cy-Cy-}} Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Cy-Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Cy-Cy-Ph FF -CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Cy-}} Cy-Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Cy-Ph FF -CF 2 O-Ph FF -F.

_{^{C 2 H 5 -Cy-Cy O}} -Ph FF -CF 2 O-Ph FF -F
_{^{C 3 H 7 -Cy-Cy OO}} -Ph FF -CF 2 O-Ph FF -F
_{^{C 4 H 9 -Cy-Cy S}} -Ph FF -CF 2 O-Ph FF -F
_{^{C 5 H 11 -Cy-Cy SS}} -Ph FF -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy-Ph-}} Ph FF -CF 2 O-Ph-F
^{_{C 5 H 11 -Cy-Ph-}} Ph FF -CF 2 O-Ph F -F
_{^{C 3 H 7 -Cy-Ph-}} Ph FF -CF 2 O- F Ph-Cl
_{^{C 5 H 11 -Cy-Ph-}} Ph FF -CF 2 O-Ph F -Cl
_{^{C 3 H 7 -Cy-Ph-}} Ph FF -CF 2 O-Ph F -CN
_{^{C 5 H 11 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -CN
_{^{C 3 H 7 -Cy-Ph-}} Ph FF -CF 2 O-Ph F -CF 3
_{^{C 5 H 11 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -CF 3
_{^{C 3 H 7 -Cy-Ph-}} Ph FF -CF 2 O-Ph F -OCF 3
_{^{C 5 H 11 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -OCF 3
_{^{C 3 H 7 -Cy-Ph-}} Ph FF -CF 2 O-Ph F -SF 5
_{^{C 5 H 11 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Ph-Ph-} CF 2 O-Ph FF -F
^{_{C 2 H 5 -Cy-Ph-}} Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Cy-Ph-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 2 H 5 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 5 H 11 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Cy-Ph-}} Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Ph-Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Cy-Ph-Ph FF -CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Cy-}} Ph-Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Ph-Ph FF -CF 2 O-Ph FF -F.

_{^{C 2 H 5 -Cy S -Ph-}} Ph FF -CF 2 O-Ph FF -F
_{^{C 3 H 7 -Cy SS -Ph-}} Ph FF -CF 2 O-Ph FF -F
_{^{C 4 H 9 -Cy O -Ph-}} Ph FF -CF 2 O-Ph FF -F
_{^{C 5 H 11 -Cy OO -Ph-}} Ph FF -CF 2 O-Ph FF -F
_{^{CH 3 -Cy-Ph F -Ph-}} CF 2 O-Ph FF -F
_{^{C 2 H 5 -Cy-Ph FF}} -Ph F -CF 2 O-Ph FF -F
_{^{CH 3 -Cy-Ph F -Ph FF}} -CF 2 O-Ph FF -F
_{^{C 2 H 5 -Cy- F Ph F}} -Ph FF -CF 2 O-Ph FF -F
_{^{C 3 H 7 -Cy-Ph FF}} -Ph FF -CF 2 O-Ph FF -F
_{^{C 4 H 9 -Cy- F Ph-}} Ph FF -CF 2 O-Ph FF -F
_{^{C 5 H 11 -Cy-Ph F}} -Ph FF -CF 2 O-Ph FF -F
_{^{CH 3 OCH 2 -Cy- F Ph FF}} -Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy-} FF Ph F -Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Cy-Ph F -Ph FF -CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Cy-}} Ph F -Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Ph F -Ph FF -CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph-F
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph F -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -SF 5
_{CH 3 -Cy-CH 2 CH 2} -Cy-Ph-CF 2 O-Ph FF -F.
_{C 2 H 5 -Cy-CH 2} CH 2 -Cy-Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Cy-CH 2 CH 2}} -Cy-Ph FF -CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-CH 2} CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-CH 2 CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} CH 2 CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Cy-Ph FF -CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph-F
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -F
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-PhF-CF 3
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Cy-CH 2} CH 2 -Ph-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Cy-} CH 2 CH 2 -Ph F -CF 2 -O-Ph FF -F
^{_{CH 3 -Cy-Cy-CH 2}} CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-Cy-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Cy-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-Cy-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} Cy-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Cy-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph-F
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph F -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-CH 2 CH 2} -Ph-Ph-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Ph-Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Cy-CH 2 CH 2}} -Ph-Ph FF -CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-CH 2 CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} CH 2 CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph-F
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -F
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Ph-CH 2} CH 2 -Ph-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Ph-} CH 2 CH 2 -Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Cy-Ph-CH 2}} CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Ph-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-Ph-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF F
_{CFH 2 CH 2 CH 2 -Cy-} Ph-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Ph-CH 2 CH 2 -Ph FF -CF 2 O-Ph FF -F.

^{_{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O-Ph-F
^{_{C 5 H 11 -Ph-Ph-}} Ph FF -CF 2 O-Ph F -F
_{^{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O- F Ph-Cl
_{^{C 5 H 11 -Ph-Ph-}} PPh FF -CF 2 O-Ph F -Cl
_{^{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O-Ph F -CN
_{^{C 5 H 11 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -CN
_{^{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O-Ph F -CF 3
_{^{C 5 H 11 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -CF 3
_{^{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O-Ph F -OCF 3
_{^{C 5 H 11 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -OCF 3
_{^{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O-Ph F -SF 5
_{^{C 5 H 11 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -SF 5.

_{CH 3 -Ph-Ph-Ph-} CF 2 O-Ph FF -F
^{_{C 2 H 5 -Ph-Ph-}} Ph F -CF 2 O-Ph FF -F
^{_{CH 3 -Ph-Ph-Ph FF}} -CF 2 O-Ph FF -F
^{_{C 2 H 5 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 4 H 9 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{C 5 H 11 -Ph-Ph-}} Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Ph-Ph FF}} -CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} -Ph-Ph FF -CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Ph-Ph-Ph FF -CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Ph-}} Ph-Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Ph} -Ph-Ph FF -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Ph-Ph-}} Ph FF -CF 2 O-Ph F -F
^{_{C 5 H 11 -Ph-Ph FF}} -Ph FF -CF 2 O-Ph FF -F
^{_{C 3 H 7 -Ph FF -Ph FF}} -Ph FF -CF 2 O-Ph F -F
^{_{C 5 H 11 -PhF-PhF-}} Ph FF -CF 2 O-Ph FF -F
_{C 3 H 7 -Ph-Ph-} CH 2 CH 2 -Ph FF -CF 2 O-Ph F -F
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph-Ph FF -CF 2 O-Ph FF -F.

As the compound (2a-4), the following compounds are preferable.
_{C 3 H 7 -Ph-CF 2} O-Ph-Ph F -F
^{_{C 5 H 11 -Ph F -CF 2}} O-Ph-Ph FF -F
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph-Ph F -F
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph-Ph FF -F
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph F -Ph F -F
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph FF -Ph FF -F
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph-Ph F -CN
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph-Ph FF -CN
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph-Ph F -CF 3
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph-Ph FF -CF 3
^{_{C 3 H 7 -Ph FF -CF 2}} O-Ph-Ph F -OCF 3
^{_{C 5 H 11 -Ph FF -CF 2}} O-Ph-Ph FF -OCF 3.

As the compound (2a-5), the following compounds are preferable.
_{C 3 H 7 -Cy-Ph-} CF 2 O-Ph-Ph F -F
^{_{C 5 H 11 -Cy-Ph F}} -CF 2 O-Ph-Ph FF -F
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph-Ph F -F
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph-Ph FF -F
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph F -Ph F -F
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph FF -Ph FF -F
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph-Ph F -CN
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph-Ph FF -CN
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph-Ph F -CF 3
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph-Ph FF -CF 3
^{_{C 3 H 7 -Cy-Ph FF}} -CF 2 O-Ph-Ph F -OCF 3
^{_{C 5 H 11 -Cy-Ph FF}} -CF 2 O-Ph-Ph FF -OCF 3.

_{C 3 H 7 -Ph-Ph-} CF 2 O-Ph-Ph F -F
^{_{C 5 H 11 -Ph-Ph F}} -CF 2 O-Ph-Ph FF -F
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph-Ph F -F
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph-Ph FF -F
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph F -Ph F -F
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph FF -Ph FF -F
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph-Ph F -CN
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph-Ph FF -CN
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph-Ph F -CF 3
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph-Ph FF -CF 3
^{_{C 3 H 7 -Ph-Ph FF}} -CF 2 O-Ph-Ph F -OCF 3
^{_{C 5 H 11 -Ph-Ph FF}} -CF 2 O-Ph-Ph FF -OCF 3.

As the compound (2a-6), the following compounds are preferred.
_{C 3 H 7 -Cy-CF 2} O-Ph-F
_{C 5 H 11 -Cy-CF 2} O-Ph F -F
_{C 3 H 7 -Cy-CF 2} O-Ph FF -F
^{_{C 3 H 7 -Cy-CF 2}} O- F Ph-Cl
_{C 5 H 11 -Cy-CF 2} O-Ph F -Cl
_{C 3 H 7 -Cy-CF 2} O-Ph F -CN
^{_{C 5 H 11 -Cy-CF 2}} O-Ph FF -CN
_{C 3 H 7 -Cy-CF 2} O-Ph F -CF 3
^{_{C 5 H 11 -Cy-CF 2}} O-Ph FF -CF 3
^{_{C 3 H 7 -Cy-CF 2}} O-Ph F -OCF 3
^{_{C 5 H 11 -Cy-CF 2}} O-Ph FF -OCF 3
_{C 3 H 7 -Cy-CF 2} O-Ph F -SF 5
^{_{C 5 H 11 -Cy-CF 2}} O-Ph FF -SF 5
_{C 2 H 5 -O-Cy-} CF 2 O-Ph F -F
_{CH 3 OCH 2 -Cy-CF 2} O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-CF 2 O-Ph F -F
_{CFH 2 CH 2 CH 2 -Cy-} CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -CF 2 O-Ph FF -F.

As the compound (2a-7), the following compounds are preferable.
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph-F
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph F -F
_{C 3 H 7 -Cy-Cy-} CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph F -SF 5
^{_{C 5 H 11 -Cy-Cy-}} CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Cy-CF 2} O-Ph FF -F
_{C 2 H 5 -Cy-Cy-} CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy-Cy-}} CF 2 O-Ph FF -F ··· (2a-7)
_{C 4 H 9 -Cy-Cy-} CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-Cy-} CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Cy-CF 2 O-Ph FF -F.

^{_{C 2 H 5 -Cy O -Cy-}} CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy OO -Cy-}} CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy S -Cy-}} CF 2 O-Ph FF -F
^{_{C 5 H 11 -Cy SS -Cy-}} CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph-F
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-CH 2 CH 2} -Cy-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy- (CH 2} ) 4 -Cy-CF 2 O-Ph FF -F
_{CH 3 -Cy-OCH 2 -Cy-} CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy- (CH 2} ) 4 -Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-CH 2} O-Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-OCF 2} -Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -CF 2 CF 2 -Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy- (CF 2) 4 -Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph-F
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph F -F
_{C 3 H 7 -Ph-Cy-} CF 2 O- F Ph-Cl
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph F -Cl
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph F -CN
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph FF -CN
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph F -CF 3
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph F -SF 5
^{_{C 5 H 11 -Ph-Cy-}} CF 2 O-Ph FF -SF 5.

_{CH 3 -Ph-Cy-CF 2} O-Ph FF -F
_{C 2 H 5 -Ph-Cy-} CF 2 O-Ph FF -F
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph FF -F
_{C 4 H 9 -Ph-Cy-} CF 2 O-Ph FF -F
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Ph-Cy-} CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} -Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Ph-Cy-CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Ph-}} Ph FF -CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Ph} -Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph-F
_{C 5 H 11 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Ph-CH 2} CH 2 -Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Ph-CH 2 CH 2} -Cy-CF 2 O-Ph FF -F
_{C 2 H 5 -Ph- (CH 2} ) 4 -Cy-CF 2 O-Ph FF -F
_{CH 3 -Ph-OCH 2 -Cy-} CF 2 O-Ph FF -F
_{C 2 H 5 -Ph-CH 2} CH 2 -Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Ph- (CH 2} ) 4 -Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Ph-CH 2} O-Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Ph-OCF 2} -Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} -CF 2 CF 2 -Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Ph- (CF 2) 4 -Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F.

^{_{CH 3 -Ph F -Cy-CF 2}} O-Ph FF -F
^{_{C 2 H 5 -Ph FF -Cy-}} CF 2 O-Ph FF -F
^{_{CH 3 - F Ph FF -Cy-}} CF 2 O-Ph FF -F
^{_{C 2 H 5 - F Ph-}} Cy-CF 2 O-Ph FF -F
^{_{C 3 H 7 -Ph F -Cy-}} CF 2 O-Ph FF -F
C ₄ H ₉ ^-F Ph ^F -Cy-CF ₂ O-Ph ^FF -F
^{_{C 5 H 11 -Ph FF -Cy-}} CF 2 O-Ph FF -F
^{_{C 5 H 11 -Ph FF -CF 2}} O-Cy-CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 - FF Ph F}} -Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} F -CF 2 CF 2 -Cy-CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Ph FF -Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Ph-} Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -} FF Ph-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CH 3 -Cy-CF 2 -CyF-} CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CF 2} -CyF-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-CF 2} -CyF-CF 2 O-Ph FF -F.

As the compound (2a-8), the following compounds are preferable.
_{C 3 H 7 -Cy-Cy-} Cy-CF 2 O-Ph-F
_{C 5 H 11 -Cy-Cy-} Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Cy-Cy-} Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-Cy-} Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-Cy-} Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-Cy-} Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-Cy-} Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-Cy-} Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-Cy-} Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-Cy-} Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-Cy-} Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-Cy-} Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Cy-Cy-} CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Cy-} Cy-CF 2 O-Ph FF -F
^{_{CH 3 -Cy-Cy-Ph FF}} -CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Cy-} Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-Cy-} Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-Cy-} Cy-CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-Cy-} Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-Cy-} Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Cy-Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-Cy-Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} Cy-Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Cy-Cy-CF 2 O-Ph FF -F.

^{_{C 2 H 5 -Cy-Cy O}} -Cy-CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy-Cy OO}} -Cy-CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy-Cy S}} -Cy-CF 2 O-Ph FF -F
^{_{C 5 H 11 -Cy-Cy SS}} -Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-Ph-} Cy-CF 2 O-Ph-F
_{C 5 H 11 -Cy-Ph-} Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Cy-Ph-} Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-Ph-} Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-Ph-} Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-Ph-} Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-Ph-} Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-Ph-} Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-Ph-} Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-Ph-} Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-Ph-} Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-Ph-} Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Ph-Cy-} CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Ph-} Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-Ph-} Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-Ph-} Cy-CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-Ph-} Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-Ph-} Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Ph-Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-Ph-Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} Ph-Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Ph-Cy-CF 2 O-Ph FF -F.

^{_{C 2 H 5 -Cy S -Ph-}} Cy-CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy SS -Ph-}} Cy-CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy O -Ph-}} Cy-CF 2 O-Ph FF -F
^{_{C 5 H 11 -Cy OO -Ph-}} Cy-CF 2 O-Ph FF -F
^{_{CH 3 -Cy-Ph F --Cy-}} CF 2 O-Ph FF -F
^{_{C 2 H 5 -Cy-Ph FF}} -Cy-CF 2 O-Ph FF -F
^{_{CH 3 -Cy-Ph F -Cy-}} CF 2 O-Ph FF -F
^{_{C 2 H 5 -Cy- F Ph F}} -Cy-CF 2 O-Ph FF -F
^{_{C 3 H 7 -Cy-Ph FF}} -Cy-CF 2 O-Ph FF -F
^{_{C 4 H 9 -Cy- F Ph-}} Cy-CF 2 O-Ph FF -F
^{_{C 5 H 11 -Cy-Ph F}} -Cy-CF 2 O-Ph FF -F
^{_{CH 3 OCH 2 -Cy- F Ph FF}} -Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy-} FF Ph F -Cy-CF 2 O-Ph FF -F
^{_{CH 3 CH = CHCH 2 CH 2}} -Cy-Ph F -Cy-CF 2 O-Ph FF -F
^{_{CFH 2 CH 2 CH 2 -Cy-}} Ph F -Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Ph F -Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph-F
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-CH 2 CH 2} -Cy-Cy-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-CH 2} CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-CH 2 CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} CH 2 CH 2 -Cy-Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Cy-Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph-F
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Cy-CH 2} CH 2 -Cy-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-Cy-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -Cy-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-Cy-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} Cy-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Cy-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph-F
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-CH 2 CH 2} -Ph-Cy-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{CH 3 -Cy-CH 2 CH 2} -Ph-Cy-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-CH 2 CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} CH 2 CH 2 -Ph-Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -CH 2 CH 2 -Ph-Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph-F
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Cy-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Cy-Ph-CH 2} CH 2 -Cy-CF 2 O-Ph FF -F
_{C 2 H 5 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{C 5 H 11 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Cy-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 H 2 -Cy} -Ph-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CHCH 2 CH 2} -Cy-Ph-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Cy-} Ph-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Cy} -Ph-CH 2 CH 2 -Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O-Ph-F
_{C 5 H 11 -Ph-Ph-} Cy-CF 2 O-Ph F -F
_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O- F Ph-Cl
_{C 5 H 11 -Ph-Ph-} Cy-CF 2 O-Ph F -Cl
_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O-Ph F -CN
_{C 5 H 11 -Ph-Ph-} Cy-CF 2 O-Ph FF -CN
_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O-Ph F -CF 3
_{C 5 H 11 -Ph-Ph-} Cy-CF 2 O-Ph FF -CF 3
_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O-Ph F -OCF 3
_{C 5 H 11 -Ph-Ph-} Cy-CF 2 O-Ph FF -OCF 3
_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O-Ph F -SF 5
_{C 5 H 11 -Ph-Ph-} Cy-CF 2 O-Ph FF -SF 5.

_{CH 3 -Ph-Ph-Cy-} CF 2 O-Ph FF -F
_{C 2 H 5 -Ph-Ph-} Cy-CF 2 O-Ph FF -F
_{CH 3 -Ph-Ph-Cy-} CF 2 O-Ph FF -F
_{C 2 H 5 -Ph-Ph-} Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O-Ph FF -F
_{C 4 H 9 -Ph-Ph-} Cy-CF 2 O-Ph FF -F
_{C 5 H 11 -Ph-Ph-} Cy-CF 2 O-Ph FF -F
_{CH 3 OCH 2 -Ph-Cy-} CF 2 O-Ph FF -F
_{CH 2 = CHCH 2 CH 2 -Ph} -Ph-Cy-CF 2 O-Ph FF -F
_{CH 3 CH = CH-CH 2} CH 2 -Ph-Ph-Cy-CF 2 O-Ph FF -F
_{CFH 2 CH 2 CH 2 -Ph-} Ph-Cy-CF 2 O-Ph FF -F
_{CF 2 = CHCH 2 CH 2 -Ph} -Ph-Cy-CF 2 O-Ph FF -F.

_{C 3 H 7 -Ph-Ph-} Cy-CF 2 O-Ph F -F
^{_{C 5 H 11 -Ph-Ph FF}} -Cy-CF 2 O-Ph FF -F
^{_{C 3 H 7 -Ph FF -Ph FF}} -Cy-CF 2 O-Ph F -F
^{_{C 5 H 11 -Ph F -PhF-}} Cy-CF 2 O-Ph FF -F
_{C 3 H 7 -Ph-Ph-} CH 2 CH 2 -Cy-CF 2 O-Ph F -F
_{C 5 H 11 -Ph-CH 2} CH 2 -Ph-Cy-CF 2 O-Ph FF -F.

As the compound (2a-9), the following compounds are preferred.
_{C 3 H 7 -Cy-CF 2} O-Ph-Ph F -F
_{C 5 H 11 -Cy-CF 2} O-Ph-Ph FF -F
_{C 3 H 7 -Cy-CF 2} O-Ph-Ph F -F
_{C 5 H 11 -Cy-CF 2} O-Ph-Ph FF -F
_{C 3 H 7 -Cy-CF 2} O-Ph-Ph F -CN
_{C 5 H 11 -Cy-CF 2} O-Ph-Ph FF -CN
_{C 3 H 7 -Cy-CF 2} O-Ph-Ph F -CF 3
_{C 5 H 11 -Cy-CF 2} O-Ph-Ph FF -CF 3
_{C 3 H 7 -Cy-CF 2} O-Ph-Ph F -OCF 3
_{C 5 H 11 -Cy-CF 2} O-Ph-Ph FF -OCF 3.

As the compound (2a-10), the following compounds are preferable.
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph-Ph F -F
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph-Ph FF -F
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph-Ph F -CN
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph-Ph FF -CN
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph-Ph F -CF 3
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph-Ph FF -CF 3
_{C 3 H 7 -Cy-Cy-} CF 2 O-Ph-Ph F -OCF 3
_{C 5 H 11 -Cy-Cy-} CF 2 O-Ph-Ph FF -OCF 3
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph-Ph F -F
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph-Ph FF -F
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph-Ph F -CN
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph-Ph FF -CN
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph-Ph F -CF 3
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph-Ph FF -CF 3
_{C 3 H 7 -Ph-Cy-} CF 2 O-Ph-Ph F -OCF 3
_{C 5 H 11 -Ph-Cy-} CF 2 O-Ph-Ph FF -OCF 3

  The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples. Note that fluorine gas diluted to 20% with nitrogen gas is referred to as 20% diluted fluorine gas.

  [Example 1] Synthesis example of compound (2a-2)

  Compound (1a-2) is obtained by charging compound (20) (2.5 g) in a reactor and adding aqueous sodium hydroxide solution (15 mL) in which sodium hydroxide (0.28 g) is dissolved in water (15 mL). . To this, sodium fluoride (0.6 g) was added and stirred, and 20% diluted fluorine gas (as “F”, an amount corresponding to twice the mole of compound (1a-2)) was added at a flow rate of 10 mL under ice cooling. Introduce in minutes. After the introduction, purge with nitrogen gas, add water (15 mL), and neutralize with sodium bicarbonate. The crude product was recrystallized using a mixed solvent of hexane and ethanol (mixing ratio = 1/4) and further purified by silica gel column chromatography (developing solvent = hexane) to give compound (2a-2) (1. 2 g) is obtained.

  [Example 2] Synthesis example of compound (2a-7)

  Compound (1a-7) is obtained by charging compound (30) (1.9 g) in a reactor and adding aqueous sodium hydroxide solution (12 mL) obtained by dissolving sodium hydroxide (0.22 g) in water (12 mL). . Sodium fluoride (0.5 g) is added thereto and stirred, and a fluorination reaction and post-treatment are performed in the same manner as in Example 1 to obtain compound (2a-7) (0.8 g).

The production method of the present invention can be an industrially useful production method of a difluoromethyl ether derivative useful as a liquid crystal material because it does not require a complicated separation operation and does not require special reaction conditions, reagents and the like.

Claims (3)

The compound represented by the following formula (2) is characterized by reacting a compound represented by the following formula (1) with a fluorinating agent to convert both -COOM moieties in the compound (1) into fluorine atoms. A method for producing a compound. However, the symbols in the formulas have the following meanings.
Ring group A and ring group B: each independently represents a carbocyclic group which may contain a hetero atom as an atom constituting the ring, and a hydrogen atom in the group may be substituted with a halogen atom.
R ^a : a monovalent organic group.
R ^b : a monovalent organic group, a hydrogen atom, a halogen atom (b), a cyano group, or —SF ₅ .
M: a hydrogen atom or an alkali metal atom.

  The cyclic group A and the cyclic group B are each independently a 1,4-phenylene group (one or two hydrogen atoms in the group may be substituted with a fluorine atom) or trans-1,4- The production method according to claim 1, which is a cyclohexylene group. The production method according to claim 1 or 2, wherein the fluorinating agent is xenon difluoride or fluorine gas.