GB1078058A - Bicyclic ketones and preparation thereof - Google Patents
Bicyclic ketones and preparation thereofInfo
- Publication number
- GB1078058A GB1078058A GB4404164A GB4404164A GB1078058A GB 1078058 A GB1078058 A GB 1078058A GB 4404164 A GB4404164 A GB 4404164A GB 4404164 A GB4404164 A GB 4404164A GB 1078058 A GB1078058 A GB 1078058A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dianhydro
- bicyclic
- dinitrophenylhydrazone
- sorbose
- cis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Bicyclic ketones Chemical class 0.000 title 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- WDUVHBUZEIBPBR-PHDIDXHHSA-N (3as,6as)-3a,6a-dihydrofuro[3,2-b]furan-3,6-dione Chemical compound O1CC(=O)[C@@H]2[C@H]1C(=O)CO2 WDUVHBUZEIBPBR-PHDIDXHHSA-N 0.000 abstract 1
- DBJHHAAUYAIFCX-UYFOZJQFSA-N (3r,3ar,6as)-3-hydroxy-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one Chemical compound O1CC(=O)[C@@H]2[C@H]1[C@H](O)CO2 DBJHHAAUYAIFCX-UYFOZJQFSA-N 0.000 abstract 1
- KLDXJTOLSGUMSJ-UHFFFAOYSA-N 2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound OC1COC2C(O)COC21 KLDXJTOLSGUMSJ-UHFFFAOYSA-N 0.000 abstract 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 abstract 1
- 150000008163 sugars Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for introducing a keto group into a bicyclic, cis-linked 5-membered ring system comprises reacting a bicyclic, cis-linked 5-membered ring compound containing at least one endo secondary hydroxyl group with oxygen in the presence of at least about 5% by weight, based on the weight of the starting material, of a noble metal catalyst, e.g. Pt. Specified starting materials are 1,4:3,6-dianhydrohexitols of formula <FORM:1078058/C2/1> Exo-hydroxyl groups are unaffected. Examples prepare 1,4:3,6-dianhydro-D-threo-2,5-hexo-diulose and its bis-2,4-dinitrophenylhydrazone, 1,4:3,6 - dianhydro - D - fructose and its 2,4-dinitro - phenylhydrazone and 1,4:3,6 - dianhydro - L - sorbose and its 2,4 - dinitrophenylhydrazone and p-tolylsulphonylhydrazone, the sugars beig claimed per se. 1,4:3,6 - Dianhydro - L - sorbose is reduced with sodium amalgam to give 1,4:3,6-dianhydro - D - sorbitol and 1,4:3,6 - dianhydro-L-iditol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA0044461 | 1963-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1078058A true GB1078058A (en) | 1967-08-02 |
Family
ID=6934216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4404164A Expired GB1078058A (en) | 1963-11-02 | 1964-10-28 | Bicyclic ketones and preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1443385B1 (en) |
| GB (1) | GB1078058A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009000661A1 (en) | 2009-02-06 | 2010-08-12 | Evonik Degussa Gmbh | Preparing (1S,5S)-2,6-dioxabicyclo-(3.3.0)-octan-4,8-dione, comprises oxidizing dianhydrohexitols or their corresponding hydroxy ketones with oxygen-containing gas in the presence of catalyst composition containing e.g. a nitroxyl radical |
-
1963
- 1963-11-02 DE DE19631443385 patent/DE1443385B1/en active Pending
-
1964
- 1964-10-28 GB GB4404164A patent/GB1078058A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1443385B1 (en) | 1970-04-30 |
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