Diphenylmethylphosphine oxide

P-Oxidation. P-oxidation, a little known reaction, involves the conversion of trisub-stituted phosphines to phosphine oxides, for example, diphenylmethylphosphine to diphenylmethylphosphine oxide. Although this reaction is described as a typical CYP-dependent monooxygenation, it too is now known to be catalyzed by the FMO also. 

Wan, I. Y. and McGrath, J. E., Synthesis and characterization of diphenylmethylphosphine oxide containing nylon-6,6 copolymers, Abstracts of Papers of the American Chemical Society, 1995, 209(2), 119. 

Although metalation of aliphatic carbon attached to phosphorus is well documented (85,173), only recently has it been noted that the carbon-phosphorus bond in triphenylphosphine oxide can be cleaved with an equimolar amount of methyllithium at room temperature (185). Indeed, benzene is produced along with a new lithium reagent which, when hydrolyzed, gives diphenylmethylphosphine oxide in high yield (83.5%). 

This compound is a phosphine oxide derivative,with a methyl group replacing a hydrogen and two phenyl groups replacing two hydrogens. Its ncime is diphenylmethylphosphine oxide. 

P-oxidation. In an analogous manner to nitrogen and sulfur, phosphorus may also be oxidized to an oxide, as in the compound diphenylmethylphosphine. This is catalyzed by microsomal monooxygenases, both cytochromes P-450 and the FAD-requiring enzyme. 

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