Tetrahedron

Secondary phosphine oxides: The effect of structure on acid strength and rates of cleavage of disulfides

M Grayson, CE Farley, CA Streuli

Index: Grayson,M. et al. Tetrahedron, 1967 , vol. 23, p. 1065 - 1078

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Citation Number: 32

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 ...

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