Abstract
AbstractThe methoxide‐promoted elimination reaction of some 1,1,1‐trichloro‐2,2‐bis(phenyl‐substituted)ethanes (1) was investigated. The ortho‐substituted derivatives were found to be less reactive than the corresponding ortho‐unsubstituted derivatives, irrespective of the nature of their substituent. The reactivity data were correlated with the 13C NMR chemical shift values of C‐β of either 1,1,1‐trichloro‐2,2‐bis(phenyl‐substituted)ethanes or 1,1‐dichloro‐2,2‐bis(phenyl‐substituted)ethenes and the better result was obtained for the former correlation. Activation parameters for the methoxide‐promoted elimination of 1 show very similar values for ortho‐substituted derivatives. The total data set seems to be more indicative, even if not compelling, of an irreversible E1cB mechanism. Copyright © 2001 John Wiley & Sons, Ltd.
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