N-(Phenylsulfonyl)- and N-Methyl-N-(phenylsulfonyl)benzohydrazonyl Azides. Thermally Induced Cyclization to Tetrazoles and Decomposition to Benzonitriles

Article abstract of DOI:10.1246/bcsj.57.539

N-(phenylsulfonyl)- and N-methyl-N-(phenylsulfonyl)benzohydrazonoyl azides, prepared from the corresponding hydrazonoyl chlorides and sodium azide, undergo the cyclization to 5-phenyl-1-(1-phenylsulfonylamino)-1H-tetrazoles together with the competitive decomposition to benzonitriles and the Curtius-type rearrangement leading to semicarbazides when heated in benzene under reflux.The tetrazole formation of hydrazonoyl azides may be characteristic od such hydrazonoyl azides as those carrying an N-sulfonyl substituent, the strong electron-withdrawing nature of which probably promotes the cyclization.