Action of Hydrogen Bromide on Threo- and Erythro-13,14-Dihydroxybehenic Acids and the Stereochemistry of Their Mutual Transformations
✍ Scribed by Osman, S. M. ;Ahmad, Mashood
- Publisher
- John Wiley and Sons
- Year
- 1972
- Weight
- 381 KB
- Volume
- 74
- Category
- Article
- ISSN
- 0931-5985
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✦ Synopsis
Action of Hydrogen Bromide on Threo-and Erythro-l3,14-Dihydroxybehenic Acids and the Stereochemistry of Their Mutual Transformations
B y S . M . O s m a n a n d M a s h o o d A h m a d "
Threo-and erythro-13,14-dihydroxybehenic acids on treatment with hydrogen bromide in acetic anhydride yielded the erythro-and threo-~~(14)-bromo-~4(1~)-acetoxybehenic acids respectively. In addition, an abnormal reaction product has been isolated and haracterised as 13( 14)-ketobehenic acids. The studies on the stereohemica1 relationships, involved in the transformation of cis-and trans-13-docosenoic acids to their corresponding dihydroxy acids through the intermediate bromoacetoxy and epoxy acids, have led to the conclusions that support Swern's reaction scheme of the unsaturated fatty acids.