Synthesis, characterisation, and transformations of a lipid cyclic peroxide

Abstract

Photosensitised oxidation of (9E,11E)-methyl octadeca-9,11-dienoate gave an unsaturated cyclic peroxide (epidioxide) in high yield. This was characterised spectroscopically. The peroxide underwent facile rearrangement to a furanoid ester under a variety of reaction conditions. Catalytic reduction of the unsaturated peroxide cleaved the O–O bond. Bromination and epoxidation gave dibromo and epoxy esters respectively with the peroxide group still intact.