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Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides |
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| Authors: | Adrienne Fleming Mary F. Mahon Vipa Prajapati |
| Affiliation: | a Department of Applied Science and Advanced Smart Materials Research Center, Institute of Technology, Tallaght, Dublin 24, Ireland b Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, England c Department of Chemistry, National University of Ireland Maynooth, Maynooth, Co. Kildare, Ireland |
| 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-(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 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. |
| Keywords: | Tetrazole Organotin X-ray Vinyl NMR |
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