Reactions of bis(tetrazole)phenylenes:Surprising Formation of Vinyl Compounds from Alkyl halides.

Authors

Fintan Kelleher, Technological University DublinFollow
Adrienne Fleming, Technological University Dublin
Mary F. Mahon, University of Bath
John McGinley, NUI Maynooth
Vipa Prajapati, Technological University Dublin

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

Organic Chemistry, Inorganic and nuclear chemistry

Publication Details

Tetrahedron, Volume 62, Issue 39, 25 September 2006, Page 9294

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 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.

Recommended Citation

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

Funder

Irish Government