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Addition of N, N-Dibromobenzene Sulfonamide to a Terminal Olefinic Fatty Acid I

✍ Scribed by Ahmad, F. ;Siddiqi, Nasirullah S. F. ;Osman, S. M.

Publisher
John Wiley and Sons
Year
1980
Weight
391 KB
Volume
82
Category
Article
ISSN
0931-5985

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✦ Synopsis

Abstract

Reaction of N,N‐dibromobenzene sulfonamide (NNDBS) with terminal olefinic fatty acid methyl ester (methyl undecenoate) afforded a mixture of one major and two minor compounds as revealed by TLC. Isolation and purification of the individual compounds were achieved by column chromatography. IR and NMR spectral studies characterised these to be methyl 10‐bromo‐11‐(N‐benzene sulfonamido)‐undecanoate, methyl 10,11‐dibromoundecanoate and methyl 10‐bromo‐11‐hydroxyundecanoate. Benzene sulfonamide adduct has been cyclized with base to N‐sulfonylaziridine. Ring opening of aziridine with sodium methoxide finally yielded methyl 10‐(N‐benzene sulfonamido)‐11‐methoxy undecanoate.

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Selective terminal olefin oxidation of n
Selective terminal olefin oxidation of n-3 polyunsaturated fatty acids
✍ Tadahiro Kato; Toshifumi Hirukawa; Kohji Namiki 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 214 KB

Through the action of N-bromosuccinimide in aqueous glyme, terminal double bond of n-3 fatty acids was selectively converted to the corresponding bromohydrin. This evidence suggests the tight conformation of the n-3 fatty acids in aqueous medium.