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Reaction of Terminal and Non-terminal Dihydroxy Fatty Acids with Hydrogen Bromide

✍ Scribed by Osman, S. M. ;Qazi, G. A. ;Siddiqi, I. A.

Book ID
102932336
Publisher
John Wiley and Sons
Year
1975
Weight
503 KB
Volume
77
Category
Article
ISSN
0931-5985

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✦ Synopsis

Abstract

The action of hydrogen bromide on non‐terminal glycol acids (threo and erythro‐6,7‐dihydroxystearic acids) leads to the formation of 6(7)–7(6)‐bromoacetoxystearic and 6(7)‐ketostearic acids as major and minor products of the reaction. On the other hand the same reaction on a terminal glycol acid, 10,11‐dihydroxyundecanoic yielded only one bromoacetoxy acid (10‐acetoxy‐11‐bromoundecanoic) and a diacetoxy derivative (10,11‐diacetoxyundecanoic) as minor and major products. Assignment of configuration and structures of reaction products are based on the I. R., N. M. R. and mass spectral studies. It is evident that hydrogen bromide reaction of the terminal glycol acid takes a different course from that observed in the nonterminal dihydroxy acids.

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