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Fatty acids, part 18. An addition reaction of methyl linoleate accompanied by cyclisation

Authors
Journal
Chemistry and Physics of Lipids
0009-3084
Publisher
Elsevier
Publication Date
Volume
2
Issue
2
Identifiers
DOI: 10.1016/0009-3084(68)90024-8

Abstract

Abstract Radical addition of acetic anhydride to methyl linoleate yields telomer, 1:2-adducts, and saturated and unsaturated 1:1-adducts. The unsaturated 1:1-adduct is probably a, mixture of the four expected products with the side chain attached at C(9), C(10), C(12), or C(13). This conclusion is based on comparison of the reaction product with methyl- 9-(carbomethoxymethyl)-octadec-12-enoate and methyl 12-(carbomethoxymethyl)-octadec 9-enoate, prepared from the corresponding hydroxy esters by malonation of their mesylates. It is concluded that in the saturated 1:1-adduct the unsaturated five carbon unit of methyl linoleate has been cyclised giving cyclopentane and/or cyclobutane compounds.

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