Tetrahedron p. 2899 - 2902 (1985)
Update date:2022-08-17
Topics:
Cardinale, G.
Laan, J. A. M.
Ward, J. P.
A general method is described for the conversion of (mono)alkenic esters with the double bond at the nth 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.
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