Enol esters. VII. Isolation and rearrangement of terminal fatty oxirane esters

Isopropenyl esters of mono‐ and dibasic fatty acids were epoxidized with m‐chloroperbenzoic acid in carbon tetrachloride. The isolation of the resulting oxirane ester was difficult because of the spontaneous rearrangement to a hydroxyacetone ester. Rapid gel filtration was the only method that consistently afforded good yields of the oxiranes. The infrared spectra of these oxirane esters had many strong, sharp bands which were completely lacking in the rearranged product. The isomerization, carried out in several ways, could easily be followed spectrally and a qualitative estimate of purity made.