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Elimination Reactions of Stilbene Dibromides. Dehydrobromination by Acetate, Cyanide or Chloride Ions in Dimethylformamide
Avraamides, James,Parker, Alan J.
, p. 1705 - 1717 (2007/10/02)
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 (E 2H) or Cα(E2C).The slowest reaction in with chloride ion, which also gives the highest anti/syn elimination product ratio.
