Title of article :
Brown Selectivity Disobedience of Hyperdeaminative Friedel-Crafts Benzylation: Electrophilic Aromatic Substitutions via Hyperdeaminatively Generated Benzyl Carbocations
Author/Authors :
Darbeau, R.W. McNeese State University - Department of Chemistry, USA , Siso, L.M. McNeese State University - Department of Chemistry, USA , Trahan, G.A. McNeese State University - Department of Chemistry, USA , Nolan, R.S. McNeese State University - Department of Chemistry, USA
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.
Keywords :
Hyperdeamination , deamination , Brown selectivity relationship , Friedel , Crafts , benzylation
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
