Reactivity of 7-halogeno-4-nitrobenzofurazans towards thiophenols. A kinetic investigation

Abstract

The reactions of 7-chloro- and 7-bromo-4-nitrobenzofurazan with thiophenols in methanol afford the products of arylthiodehalogenation together with the corresponding hydrogen halide. Kinetic analysis indicates a remarkable auto-inhibition which has been interpreted on the basis of two competitive mechanisms, one due to the ionized and the other to the un-ionized thiophenol. The substituent effect in the thiophenol for the two mechanisms is discussed.