STUDIES ON THE THERMAL DECARBOXYLATION OF 1-ALKOXYCARBONYLBENZOTRIAZOLES

1-Alkoxycarbonylbenzotriazoles on thermolysis lose carbon dioxide; the decarboxylation is accompanied by the formation of a mixture of 1- and 2-alkylbenzotriazoles, with the N-1 isomer predominating over the N-2 isomer in all cases. A cross-over experiment, in which heating equimolar amounts of 1-benzyloxycarbonylbenzotriazole and 1-(4-methylbenzyloxycarbonyl)-5,6-dimethylbenzotriazole gave almost all the cross-over products, supports the proposed intermolecular mechanism for this decarboxylation and the formation of 1- and 2-alkylbenzotriazoles, No decarboxylation was observed for 1-phenoxycarbonylbenzotriazole.