Bismuth(III)-catalyzed oxidative cleavage of aryl epoxides: substituent effects on the kinetics of the oxidation reaction

Article abstract of DOI:10.1016/0022-328X(94)88192-8

Bismuth(III)mandelate catalyzes the oxidative C-C bond cleavage of a series of styrene epoxides in DMSO, to the corresponding aryl carboxylic acids.The reaction is accelerated in the presence of electron-donating groups substituting the phenyl ring.A good Hammet correlation of log k_obs versus ? has been obtained, with a ρ of -1.08.Key words: Bismuth; Aryl epeoxide cleavage; Oxidation; Substituent effects; Bi(III) catalysis; Hammet correlation