William B. Farnham

Kinetics of retro-cyanoethylation of phosphonium salts and the question of phosphole aromaticity

Phospholium ion (1) is cleaved by sodium methoxide into 1,2,5-triphenylphosphole and acrylonitrile at a rate substantially greater than that observed for comparable phosphonium ions, a finding which is consistent with significant delocalization of the lone electron pair on phosphorus in phospholes.

Stereochemistry of methanolysis of menthyl S-methyl phenylphosphonothioate

Contrary to expectation, displacement of the thiomethyl group in menthyl S-methyl phenylphosphonothioate by methoxide ion occurs with inversion of configuration at phosphorus.

The absolute configuration of menthyl methylphosphinate: a reassignment and its stereochemical consequences

The absolute configurations of the epimeric menthyl methylphosphinates (1) are the reverse of those previously reported, and the stereochemistry of reactions which depend on (1) for a configurational anchor is reassessed in the light of this finding.

Stereospecific free-radical addition of menthyl phenylphosphinate to cyclohexene: evidence for retention of configuration at phosphorus

In contradistinction to a recent report that the free-radical addition of menthyl methylphosphinate to alkenes proceeds with inversion of configuration at phosphorus, dibenzoyl peroxide-catalysed addition of menthyl phenylphosphinate to cyclohexene occurs with retention of configuration.