PREPARATION OF TERMINAL ALKENIC ESTERS BY AN OXIDATIVE RADICAL REACTION

Article abstract of DOI:10.1016/S0040-4020(01)96613-X

A general method is described for the conversion of (mono)alkenic esters with the double bond at the n^th C atom to terminal alkenic esters of (n-1) C atoms in length, with the double bond at n-2.Ozonolysis, either in methanol or in light petroleum, is followed by reaction with a mixture of ferrous and cupric salts.Methyl 10-undecenoate, methyl oleate (methyl (Z)-9-octadecenoate) and methyl erucate (methyl (Z)-13-docosenoate) were converted to methyl 8-nonenoate, methyl 7-ocotenoate and methyl 11-dodecenoate respectively.An improved preparation of 5-hexenoic acid is also described.