RU2008106385A - METHOD FOR PRODUCING TRICYCLO [2.4.1.02,5] -NONAN-3-SPIRO-1'-BUTANE - Google Patents
METHOD FOR PRODUCING TRICYCLO [2.4.1.02,5] -NONAN-3-SPIRO-1'-BUTANE Download PDFInfo
- Publication number
- RU2008106385A RU2008106385A RU2008106385/04A RU2008106385A RU2008106385A RU 2008106385 A RU2008106385 A RU 2008106385A RU 2008106385/04 A RU2008106385/04 A RU 2008106385/04A RU 2008106385 A RU2008106385 A RU 2008106385A RU 2008106385 A RU2008106385 A RU 2008106385A
- Authority
- RU
- Russia
- Prior art keywords
- tricyclo
- nonane
- hexane
- spiro
- et3al
- Prior art date
Links
- 239000001273 butane Substances 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims abstract 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract 5
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000012300 argon atmosphere Substances 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 229910007926 ZrCl Inorganic materials 0.000 claims 3
- FFOAJLYBPRZQNS-UHFFFAOYSA-N 3-methylidenetricyclo[4.2.1.02,5]nonane Chemical compound C1CC2C3CC(=C)C3C1C2 FFOAJLYBPRZQNS-UHFFFAOYSA-N 0.000 claims 2
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 abstract 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 abstract 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Способ получения трицикло[4.2.1.02,5]нонан-3-спиро-1'-бутана общей формулы (1) ! , ! отличающийся тем, что 3-метилентрицикло[4.2.1.02,5]нонан подвергают взаимодействию с триэтилалюминием Et3Al в присутствии катализатора цирконацендихлорида Cp2ZrCl2 в мольном соотношении 3-метилентрицикло[4.2.1.02,5]нонан:Et3Al:Ср2ZrСl2=10:(10-14):(0.4-0.6) в атмосфере аргона при температуре 20°С и нормальном давлении в гексане в течение 5-7 ч с последующим добавлением при -10°С диэтилового эфира в объеме, равном взятому гексану, трифенилфосфина Рh3P и ацетилацетоната палладия Pd(acac)2 в эквимольном к Cp2ZrCl2 количестве, затем прибавляют свежеперегнанный аллилхлорид в трехкратном избытке на взятый Еt3Аl, температуру доводят до комнатной и перемешивают еще 5 ч.The method of obtaining tricyclo [4.2.1.02,5] nonane-3-spiro-1'-butane of the general formula (1)! ! characterized in that 3-methylene tricyclo [4.2.1.02.5] nonane is reacted with Et3Al triethylaluminium in the presence of a Cp2ZrCl2 zirconacide dichloride catalyst in a molar ratio of 3-methylene tricyclo [4.2.1.02.5] nonane: Et3Al: Сp2ZrСl2 = 10: (10-14 ) :( 0.4-0.6) in an argon atmosphere at a temperature of 20 ° C and normal pressure in hexane for 5-7 hours, followed by the addition of diethyl ether at -10 ° C in a volume equal to that of hexane, triphenylphosphine Ph3P and palladium Pd acetylacetonate ( acac) 2 in an amount equimolar to Cp2ZrCl2, then freshly distilled allyl chloride is added in triplicate SG taken in excess Et3Al, brought to room temperature and stirred for another 5 h.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2008106385/04A RU2373174C1 (en) | 2008-02-18 | 2008-02-18 | Method of producing tricyclo[4,2,1,02,5]-nonane-3-spiro-1'-butane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2008106385/04A RU2373174C1 (en) | 2008-02-18 | 2008-02-18 | Method of producing tricyclo[4,2,1,02,5]-nonane-3-spiro-1'-butane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008106385A true RU2008106385A (en) | 2009-08-27 |
| RU2373174C1 RU2373174C1 (en) | 2009-11-20 |
Family
ID=41149320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008106385/04A RU2373174C1 (en) | 2008-02-18 | 2008-02-18 | Method of producing tricyclo[4,2,1,02,5]-nonane-3-spiro-1'-butane |
Country Status (1)
| Country | Link |
|---|---|
| RU (1) | RU2373174C1 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU791718A1 (en) * | 1979-03-26 | 1980-12-30 | Ленинградский Ордена Ленина И Ордена Трудового Красного Знамени Государственный Университет Им.А.А.Жданова | Bicyclo-/1,1,0/-butanedi-(spirocycloburane) and its preparation method |
| US5710299A (en) * | 1996-06-27 | 1998-01-20 | Albemarle Corporation | Production of bridged metallocene complexes and intermediates therefor |
-
2008
- 2008-02-18 RU RU2008106385/04A patent/RU2373174C1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2373174C1 (en) | 2009-11-20 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20100219 |