Reduction of Aromatic Ketones or Thioketones with Phenylphosphine

Abstract

Abstract Reactions of certain aromatic ketones or thioketones with phenylphosphine and subsequent addition of diethyl disulfide gave the reduction products of the ketones and S,S-diethyl phenylphosphonodithioate or S,S-diethyl phenylphosphonotrithioate. A possible intermediate of the phosphine moiety was suggested to be phenylphosphinylidene [PhP=O] or phenylphosphinothioylidene [PhP=S]. The reduction of 10,10′-bianthrone and Δ10,10′-bianthrone resulted in the cleavage of the carbon–carbon single and double bonds and the reduction of the carbonyl groups, respectively.