Chemistry Letters, Vol.32, No.11, 1080-1081, 2003
Reaction of stable sulfenic and selenenic acids containing a bowl-type steric protection group with a phosphine. Elucidation of the mechanism of reduction of sulfenic and selenenic acids
The mechanism of the reduction of the stable sulfenic acid 1 and selenenic acid 2 containing a bowl-type steric protection group by triphenylphosphine was elucidated by tracer studies using (H2O)-O-18. It was found that the initial step of the reaction involves the attack of the phosphine on the sulfur or selenium atom of 1 and 2, respectively, in contrast with the reduction of hydroperoxides by a phosphine, where the initial attack occurs on the hydroxylic oxygen.