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Kinetic study of methoxide‐promoted elimination reactions of some 1,1,1‐trichloro‐2,2‐bis(phenyl‐substituted)ethanes
Author(s) -
Fontana Gianfranco,
Frenna Vincenzo,
Lamartina Liliana,
Natoli Maria Concetta,
Noto Renato
Publication year - 2002
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.459
Subject(s) - chemistry , methoxide , substituent , reactivity (psychology) , medicinal chemistry , sodium methoxide , reductive elimination , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The 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 13 C 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 E 1 cB mechanism. Copyright © 2001 John Wiley & Sons, Ltd.