Fatty acids, part 21: The rearrangement of methyl 12, 13-epoxyoleate by boron trifluoride with formation of cyclopropane esters

✍ Scribed by H.B.S. Conacher; F.D. Gunstone

• Book ID: 103039267
• Publisher: Elsevier Science
• Year: 1969
• Tongue: English
• Weight: 741 KB
• Volume: 3
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(69)90013-9

✦ Synopsis

Yreated ~ ~th boron mfluorlde etherate m dloxan soluhon, methyl 12,13-epoxyoleate gl,~es the 12-and 13-oxo-oleates as major products These are accompamed by cyclopropane compounds (8-1 I o,,) which are mainly the ~ ts and tran ~ isomers of methyl 9,10-methylene-12-oxo-heptadecanoate [I-(7'-carbomethoxi~hept~l), 2-(2'-oxohept~l)cyclopropane] In benzene solution the cyclopropanes are formed in higher yield (38 "o) The structure of long-chain cyclopropane esters can be determined bs, oxldahon with chromic acid * Part 20, Chem Phys Liplds 3 (1969) 191-202 * Present address Food and Drug Dwectorate