Electrophilic aromatic trichloromethylation: intermediates and products |
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| Authors: | Belen" kii,L. I.,Chuvylkin,N. D.,Suslov,I. A. |
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| Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117991 Moscow, Russian Federation;(2) Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125820 Moscow, Russian Federation |
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| Abstract: | Based on analysis of experimental data for reactions in solutions and in the gas phase and on the results of quantum-chemical calculations, it was shown that rearomatization stage of cationic  -complexes formed in the electrophilic trichloromethylation is not deprotonation but dehydrochlorination to form aryldichlorocarbenium ions that are the real products of the reaction under consideration. The geometries and electronic structures of phenyldichlorocarbenium and mesityldichlorocarbenium ions were studied and differences in their reactivities were discussed. |
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| Keywords: | electrophilic trichloromethylation mechanism intermediates (trichloromethyl)arenium ions aryldichlorocarbenium ions trichloromethylarenes |
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