Elimination reactions of stilbene dibromides. Dehydrobromination by acetate, cyanide or chloride ions in dimethylformamide
Keyword(s):
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.
1971 ◽
Vol 93
(2)
◽
pp. 511-512
◽
1994 ◽
Vol 269
(51)
◽
pp. 32306-32312