Preparation of azides from hydrazines by using dinitrogen tetroxide as nitrosonium ion source

Abstract

Various hydrazines such as aryl-, carbonyl-, and sulfonyl-hydrazine were reacted with dinitrogen tetroxide to give the corresponding azides in excellent yields under mild conditions at low temperature (−20–−40°C) in acetonitrile. The reaction appears to be initiated by formation of the β-nitroso hydrazine intermediate which converts into the azide product.