Rogue Scholar

Published December 6, 2013 in Henry Rzepa's Blog

Text books will announce that during aromatic electrophilic substitution, aromaticity is lost by the formation of a Wheland intermediate (and regained by eliminating a proton). Is that entirely true?

References

General Chemistry

A Different Story of π-DelocalizationThe Distortivity of π-Electrons and Its Chemical Manifestations

https://doi.org/10.1021/cr990363l

Published April 12, 2001 in Chemical Reviews

Authors Sason Shaik, Avital Shurki, David Danovich, Philippe C. Hiberty

Colloid and Surface ChemistryBiochemistryGeneral ChemistryCatalysis

Stable carbonium ions. IC. Benzenonium ion (C6H7+) and its degenerate rearrangement

https://doi.org/10.1021/ja00711a057

Published April 1, 1970 in Journal of the American Chemical Society

Authors George A. Olah, Richard H. Schlosberg, David P. Kelly, Gh. D. Mateescu

Colloid and Surface ChemistryBiochemistryGeneral ChemistryCatalysis

Stable carbocations. CXXIV. Benzenium ion and monoalkylbenzenium ions

https://doi.org/10.1021/ja00761a041

Published March 1, 1972 in Journal of the American Chemical Society

Authors George A. Olah, Richard H. Schlosberg, Richard D. Porter, Y. K. Mo, David P. Kelly, Gheorghe D. Mateescu

Does forming a Wheland intermediate disrupt all aromaticity?

References

A Different Story of π-DelocalizationThe Distortivity of π-Electrons and Its Chemical Manifestations

Stable carbonium ions. IC. Benzenonium ion (C6H7+) and its degenerate rearrangement

Stable carbocations. CXXIV. Benzenium ion and monoalkylbenzenium ions