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)

Friedel-Crafts alpha-phenylethylation of benzene and toluene was compared with beta-phenylethylation and showed a low ratio of ortho/para substitution with only 2-3% meta isomer formation with kt/kb rate ratios between 58 and 76. Data indicate late arenium ion (sigma complex)-like transition states.

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 1992-02, Vol.89 (3), p.915
Main Authors: Olah, George A, Hamanaka, Sawako
Format: Article
Language:English
Subjects:
Biochemistry
Online Access:Get full text
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Summary:Friedel-Crafts alpha-phenylethylation of benzene and toluene was compared with beta-phenylethylation and showed a low ratio of ortho/para substitution with only 2-3% meta isomer formation with kt/kb rate ratios between 58 and 76. Data indicate late arenium ion (sigma complex)-like transition states.
ISSN:0027-8424
1091-6490