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

✍ Scribed by F.D. Gunstone; R.G. Powell

• Publisher: Elsevier Science
• Year: 1968
• Tongue: English
• Weight: 426 KB
• Volume: 2
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(68)90024-8

✦ Synopsis

Radical addition of acetic anhydride to methyl linoleate yields telomers, 1:2-adducts, and saturated and unsaturated l:l-adducts. The unsaturated l:l-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 malona.tion 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.