Bulletin of the Chemical Society of Japan

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

S Ito, Y Tanaka, A Kakehi

Index: Ito, Suketaka; Tanaka, Yumo; Kakehi, Akikazu Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 2 p. 539 - 543

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Citation Number: 7

Abstract

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-(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 ...