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Organic Chemistry, Inorganic and nuclear chemistry
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-(Bu3SnN4C)2C6H4 (4), 1,3-(Bu3SnN4C)2C6H4 (5) and 1,4-(Bu3SnN4C)2C6H4 (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 and 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.
Kelleher, F., Fleming, A., Mahon, M.F., McGinley, J., Prajapati, V.: Reactions of bis(tetrazole)phenylenes:Surprising Formation of Vinyl Compounds from Alkyl halides.. Tetrahedron, vol. 62 (39), 25 September 2006, p. 9294