Thermal Decomposition of Arenediazonium Tetrafluoroborates in Nitromethane

Abstract

Thermal decomposition of several arenediazonium tetrafluoroborates in nitromethane gave the corresponding phenols as the main products, accompanying the corresponding fluorinated benzenes and benzoxazoles. The oxygen atom of the hydroxyl group of the products was proved to arise from nitromethane. Product analyses, kinetic results of the decomposition reaction, and the analyses of isomer distribution of products in the reaction of aromatic substrate with the diazonium salt suggested that the decomposition proceeded heterolytically, via aryl cation intermediates. In the decomposition of the p-methoxy derivative, however, a competition between heterolytic and homolytic pathways was suggested.