PMID: 11607274Feb 1, 1992Paper

Friedel-Crafts phenylethylation of benzene and toluene with alpha- and beta-phenylethyl chlorides: pi-aryl participation in polarized donor-acceptor beta-phenylethylating complexes distinct from phenonium ions (sigma complexes)

Proceedings of the National Academy of Sciences of the United States of America
George A OlahJ A Olah

Abstract

Friedel-Crafts alpha-phenylethylation of benzene and toluene, compared with beta-phenylethylation, shows a low ratio of ortho/para substitution with only 2-3% meta isomer formation, with kT/kB rate ratios between 58 and 76. The data indicate late arenium ion (sigma complex)-like transition states. beta-Phenylethylation in contrast gives low kT/kB rate ratios with a substantially higher ortho/para isomer ratio of 17-21% for the meta substituent. Experimental evidence points to thermodynamically controlled isomerizations effecting results. The data also indicate formation of an oriented pi-complex involving phenyl participation (as contrasted with complete phenonium ion formation) in the alkylation intermediates of the beta-phenylethylation reactions.

Citations

Feb 24, 2001·Genome Génome / Conseil National De Recherches Canada·S KuhnW Traut
May 3, 2000·Genome Génome / Conseil National De Recherches Canada·A PavesiF M Restivo
May 3, 2000·Genome Génome / Conseil National De Recherches Canada·V SievertW Traut
Mar 19, 2015·The Journal of Organic Chemistry·Yin-Long LiJun Deng

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