Abstract
Second order rate constants for reaction of a series of symmetrical, substituted diaryl-phosphine oxides and several dialkyphosphine oxides with diphenyl disulfide and acidities of the former in t-butanol and 95% ethanol were measured. Catalysis of the disulfide cleavage by base was observed. Correlation with Hammett substituent constants of both rate and acidity data is reported. A mechanism in which a rapid equilibrium “enolization” of the nucleophilic secondary phosphine oxide group occurs prior to cleavage of the disulfide bond is proposed. The reaction was reversible in the presence of triethylamine.
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