Cyclopropyl epoxides. Reactions of some αβ-dibromoketones with dimethyloxosulphonium methylide

Abstract

2,3-Dibromo-3-phenylpropiophenones eliminated both bromine and hydrogen bromide on reaction with dimethyloxosulphonium methylide (DMOSM); the resulting αβ-unsaturated ketones formed cyclopropyl ketones which, when suitably substituted, continued to react with DMOSM, forming a variety of heterocyclic products. A contiguous cyclopropyl epoxide underwent ring-opening oxymercuriation with mercuric acetate via 5-oxypent 2-en-1-ols. A cyclopropylcyclopropane analogue of the epoxide was stable at 300 °C.