Studies on the hypohalogenation of isomeric 6,7-octadecenoic acids: Petroselinic and petroselaidic acids

✍ Scribed by M. O. Farooq; S. M. Osman; M. Saleem Siddiqui

• Book ID: 104586314
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 370 KB
• Volume: 80
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19610800409

✦ Synopsis

Abstract

The 6(7)‐chloro‐7(6)‐hydroxystearic acids of petroselinic and petroselaidic acids have been successfully prepared by the action of hypochlorous acid on the parent acids and by the hydrochlorination of their corresponding epoxides. The chlorohydrins on dehydrohalogenation furnished the original epoxides. The bromohydrins and iodohydrins have been prepared and were found to behave in a similar manner. The mutual transformation of the erythro‐ and threo‐6, 7‐dihydroxystearic acids through the chlorohydrins and the epoxides has been achieved.

The results of these experiments lead to the conclusion that inversions of configuration occur during the replacement of the hydroxyl group by a halogen atom and also at the time of the opening and closing of the epoxide ring.