Clemmensen reduction. Part 6. The synthesis of cyclopropane-1,2-diyl diacetates

Abstract

The synthesis of a number of cyclopropane-1,2-diyl diacetates is reported. Non-enolisable 1,3-dicarbonyl compounds are converted to cyclopropane-1,2-diyl diacetates by reduction with amalgamated zinc powder and dry hydrogen chloride in diethyl ether containing acetic anhydride or acetyl chloride. Enolisable 1,3-diketones give cyclic diol diacetates only when the diketo-component of the tautomeric mixture is high, otherwise enol acetates and other compounds are produced. 1H and 13C N.m.r. Spectra are reported and discussed.