TY - JOUR
T1 - Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides
AU - Fleming, Adrienne
AU - Kelleher, Fintan
AU - Mahon, Mary F.
AU - McGinley, John
AU - Prajapati, Vipa
PY - 2005/7/18
Y1 - 2005/7/18
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-(Bu3SnN 4C)2C6H4 (4), 1,3-(Bu 3SnN4C)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 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.
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-(Bu3SnN 4C)2C6H4 (4), 1,3-(Bu 3SnN4C)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 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.
KW - NMR
KW - Organotin
KW - Tetrazole
KW - Vinyl
KW - X-ray
UR - https://www.scopus.com/pages/publications/20444440794
U2 - 10.1016/j.tet.2005.05.013
DO - 10.1016/j.tet.2005.05.013
M3 - Article
AN - SCOPUS:20444440794
SN - 0040-4020
VL - 61
SP - 7002
EP - 7011
JO - Tetrahedron
JF - Tetrahedron
IS - 29
ER -