Acid hydrolysis of colchicine and related compounds.

Acid-catalyzed hydrolysis of the methox-ytropone moiety of colchicine has been shown to proceed at a greater rate than in the case of isocolchicine1. (Struc­ tures are shown in Table I.) No interpretation of this rate difference has been offered. And, while a mecha­ nism for the acid-catalyzed hydrolysis of 2 -methoxytropone has been proposed2, no kinetic data on this type of reaction either for simple methoxytropones or on colchicine type compounds have been reported. Thus, the present investigation was undertaken to examine the effect of structural changes on the rate of acid hydrolysis of colchicine and to examine certain kinetic aspects of this reaction.