Evaluation of electrophilic activities of substituted nitroarenes in the VNS reaction with secondary and tertiary carbanions
Relative electrophilic activities of substituted nitroarenes in the vicarious nucleophilic substitution (VNS) reaction with carbanion of chloromethylp-chlorophenyl and bromomethyl phenyl sulfones, 1 and 2, were determined via competitive experiments. The results are in good agreement with relative activities determined earlier in the competitive experiments with carbanion of chloromethyl phenyl sulfone 3 confirming reliability of these data. On the other hand, analogous competitive experiments with tertiary carbanions of chloroform and 1-chloroethyl phenyl sulfone gave results much affected by steric effects thus the VNS reaction with these carbanions cannot be used for evaluation of electrophilic activities of nitroarenes.
Blazej,Wilenska,Voynova,Makosza
p. 2017 - 2030
(2008/12/23)
SYNTHESIS, SPECTRAL STUDIES AND C-S BOND FISSION OF SOME NOVEL ALKYL -3-NITROBENZOATES AND THEIR SULFINYL DERIVATIVES
Methyl and ethyl-4--3-nitrobenzoates and the corresponding sulfinyl derivatives have been synthesized.The structure of these esters were proved by IR, NMR and mass spectra.A linear relationship between δ-ppm values of the benzylic protons and ?-Hammett values of the 4'-substituents has been found.The carbon-sulfur bond fission with 5percent sodium hydroxide solution in addition to the alkaline ester hydrolysis is discussed. Key words: Arylsulfonyl; arylsulfinyl nitrobenzoate; NMR; mass spectra; C-S bond fission.
El-Bardan, Ali A.
p. 153 - 164
(2007/10/02)
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