Reduction of Ozonides by Means of Polymeric Triphenylphosphine: Simplified Synthesis of Carbonyl Compounds from Alkenes

Abstract

A classical system for the preparation of carbonyl compounds from alkenes relies upon ozonolysis of the double bond, followed by reductive cleavage of the ozonide so formed. Among the reagents of choice for such a reduction, triphenylphosphine certainly has enjoyed a widespread use.¹ However, in spite of the simplicity of the method, often one can face problems in the purification of the carbonyl compound from unreacted triphenylphosphine, especially if the polarities of both products are very similar. We have encountered such a problem during the preparation of the (20 S)-6β -ethoxy-3 α, 5-cyclo-5α -pregnane-20-carbaldehyde 4 from the suitably protected stigmasterol3². In this case, when triphenylphosphine was used for reduction of ozonide we never could isolate the aldehyde 2 uncontaninated by tripherylphosphine.