OXIDATION REACTIONS OF PHOSPHAALKENES.

Article abstract of DOI:10.1021/ja00350a047

Phosphaalkenes such as left bracket (2,6-dimethylphenyl) (diphenylmethylene)phosphine right bracket are quite reactive in many respects but are rather sluggish in their reaction with oxygen and sulfur. Primary intermediates in the reactions are the oxide, the phosphene and the phosphinidene oxide which together with (thio)benzophenone is formed by oxidative cleavage of the P equals C bond. The occurrence of these unstable intermediates is concluded from their interception by ethanol or water in the oxygen reactions and by ethanol in the sulfur reaction. The mechanism of these reactions and the competition between various reactants are discussed. The structure of the reaction products is determined from their spectral properties and by alternative synthesis along unequivocal routes.