Bulletin of the Chemical Society of Japan p. 539 - 543 (1984)
Update date:2022-08-05
Topics:
Ito, Suketaka
Tanaka, Yumo
Kakehi, Akikazu
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.
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