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Elimination reactions of stilbene dibromides. Dehydrobromination by acetate, cyanide or chloride ions in dimethylformamide

Avraamides, J. and Parker, A.J. (1983) Elimination reactions of stilbene dibromides. Dehydrobromination by acetate, cyanide or chloride ions in dimethylformamide. Australian Journal of Chemistry, 36 (9). pp. 1705-1717.

Link to Published Version: http://dx.doi.org/10.1071/CH9831705
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Abstract

Rates of dehydrobromination of a series of 4-nitro-and methoxystilbene dibromides by means of acetate, cyanide or chloride ions in dimethylformamide have been measured. A product analysis was performed which indicated a strong preference for anti elimination. Probable transition state structures utilized by each of the three nucleophiles are described. Attack by the base may be at either β-hydrogen (E2H) or Cα (E2C). The slowest reaction is with chloride ion, which also gives the highest anti/syn elimination product ratio.

Publication Type: Journal Article
Murdoch Affiliation: School of Mathematical and Physical Sciences
Publisher: Commonwealth Scientific and Industrial Research Organization Publishing
Copyright: © 1983 CSIRO
URI: http://researchrepository.murdoch.edu.au/id/eprint/31619
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