Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides

Abstract

The reactions of 1,2-bis(tetrazol-5-yl)benzene ( 1 ), 1,3-bis(tetrazol-5-yl)benzene ( 2 ), 1,4-bis(tetrazol-5-yl)benzene ( 3 ), 1,2-(Bu 3SnN 4C) 2C 6H 4 ( 4 ), 1,3-(Bu 3SnN 4C) 2C 6H 4 ( 5 ) and 1,4-(Bu 3SnN 4C) 2C 6H 4 ( 6 ) with 1,2-dibromoethane were carried out by two different methods in order to synthesise pendant alkyl halide derivatives of the parent bis-tetrazoles. This lead to the formation of several alkyl halide derivatives, substituted at either N1 or N2 on the tetrazole ring, as well as the surprising formation of several vinyl derivatives. The crystal structures of both 1,2-[(2-vinyl)tetrazol-5-yl)]benzene (1- N,2- N′) ( 1b ) and 1,3-bis[(2-bromoethyl)tetrazol-5-yl]benzene (2- N,2- N′) ( 5d ) are discussed.