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

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

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 2 , 2005

Become EABM
Become Reviewer


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.

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

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2005
Page: [139 - 144]
Pages: 6
DOI: 10.2174/1570178053202928
Price: $65

Article Metrics

PDF: 2