Brown Selectivity Disobedience of Hyperdeaminative Friedel-Crafts Benzylation: Electrophilic Aromatic Substitutions via Hyperdeaminatively Generated Benzyl Carbocations

Title: Brown Selectivity Disobedience of Hyperdeaminative Friedel-Crafts Benzylation: Electrophilic Aromatic Substitutions via Hyperdeaminatively Generated Benzyl Carbocations

Volume: 2 Issue: 2

Author(s): R. W. Darbeau, L. M. Siso, G. A. Trahan and R. S. Nolan

Affiliation:

Keywords: hyperdeamination, deamination, brown selectivity relationship, friedel-crafts, benzylation

Abstract: Hyperdeamination generates multiple spacer-molecule separated ion-pairs containing high-energy, relatively long-lived carbocations showing near specificity for arenes over their nascent counterions. They exhibit low intermolecular selectivity but surprisingly high intramolecular selectivity. Unlike analogous deaminative benzylations, hyperdeaminative benzylations disobey the Brown Selectivity Relationship. A model for EAS reactions with hyperactive electrophiles is proposed.

Cite this article as:

Darbeau W. R., Siso M. L., Trahan A. G. and Nolan S. R., Brown Selectivity Disobedience of Hyperdeaminative Friedel-Crafts Benzylation: Electrophilic Aromatic Substitutions via Hyperdeaminatively Generated Benzyl Carbocations, Letters in Organic Chemistry 2005; 2 (2) . https://dx.doi.org/10.2174/1570178053202928