Clemmensen reduction. Part III. αβ-Unsaturated ketones

Abstract

Further studies on the Clemmensen reduction of αβ-unsaturated ketones support the suggestion that cyclopropanols are intermediates in this reaction. A variety of approaches to, and the successful synthesis of, a hitherto unknown bicyclo[3,1,0]hexan-1-ol are described. Clemmensen reduction of cholest-4-en-3-one gives 5β-cholest-3-ene which has been synthesised by an alternative route. The behaviour of some cyclohex-2-enols under Clemmensen conditions has been investigated.