Reactions of carbonyl compounds with tervalent phosphorus reagents. Part III. The formation of olefins by deoxygenation of carbonyl compounds with diphenylphosphine oxide

Abstract

The formation of olefins from benzaldehyde or benzoylferrocene and diphenylphosphine oxide has been rationalised in terms of epoxide intermediates. These intermediates can be isolated from benzaldehyde deoxygenation reactions when the aldehyde is in excess, and it has been shown that they are readily converted into olefin by di-phenylphosphine oxide. In contrast to the benzaldehyde system, the deoxygenation of benzoylferrocene gives several products in addition to olefin and the formation of some of these is rationalised in terms of an epoxide-pathway.