Methyl 12-oxo-octadec-9-cis-enoate gave methyl 9,12-epoxyoctadeca-9,11-dienoate when treated with zinc or cadmium in the presence of di-iodomethane and 1,2-dimethoxyethane under concomitant ultrasonic irradiation, while under similar conditions copper caused cyclopropanation across the ethylenic bond in methyl oleate and ricinoleate.
M. S. F. L. K. Jie and W. L. K. Lam, J. Chem. Soc., Chem. Commun., 1987, 1460 DOI: 10.1039/C39870001460
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