TY - JOUR
T1 - Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides
AU - Fleming, A
AU - Kelleher, F
AU - Mahon, M F
AU - McGinley, J
AU - Prajapati, V
N1 - ID number: ISI:000230146400009
PY - 2005
Y1 - 2005
N2 - 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)(2)C6H4 (4), 1,3-(Bu(3)SnN(4)Q(2)C(6)H(4) (5) and 1,4-(Bu3SnN4C)(2)C6H4 (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 1,2-1(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. (c) 2005 Elsevier Ltd. All rights reserved.
AB - 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)(2)C6H4 (4), 1,3-(Bu(3)SnN(4)Q(2)C(6)H(4) (5) and 1,4-(Bu3SnN4C)(2)C6H4 (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 1,2-1(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. (c) 2005 Elsevier Ltd. All rights reserved.
U2 - 10.1016/j.tet.2005.05.013
DO - 10.1016/j.tet.2005.05.013
M3 - Article
SN - 0040-4020
VL - 61
SP - 7002
EP - 7011
JO - Tetrahedron
JF - Tetrahedron
IS - 29
ER -