The chemistry of terpenes. Part X. Oxidation of (+)-car-3-ene with chromium trioxide

Abstract

Oxidation of (+)-car-3-ene with chromium trioxide affords a range of neutral oxidation products similar to that obtained when permanganate is the oxidant. 8-Hydroxy-m-cymene is the major product when ‘unbuffered’ chromium trioxide in acetone is used. (+)-Car-3-en-2-one is formed only in traces. The ketol, (+)-3β-hydroxy-trans-caran-4-one, also a product of oxidation of (+)-car-3-ene, comprises over 80% of the neutral products of reaction of (+)-α-3,4-epoxycarane with chromium trioxide in pyridine.