Regioselective oxidation of unactivated methylene and methine groups by dry ozonation: similarity to microbiological oxidation

Abstract

Ozonation of cyclododecyl acetate or dodecyl acetate, adsorbed on silica-gel affords keto-acetates by regioselective oxidation of methylene groups remote from the binding sites; ozonation of 6-exo-acetoxy-endo,exo,-endo-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-4,9:5,8-dimethano-1H-benz[f]indane (3b) or the related ketone (3c) gives hydroxylation products similar to those obtained by microbiological hydroxylation of (3a) or (3c)