Premium
Electrophilic Alkylations in Neutral Aqueous or Alcoholic Solutions
Author(s) -
Hofmann Matthias,
Hampel Nathalie,
Kanzian Tanja,
Mayr Herbert
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200460812
Subject(s) - carbocation , nucleophile , electrophile , chemistry , aqueous solution , friedel–crafts reaction , computational chemistry , ion , organic chemistry , substitution reaction , nucleophilic substitution , photochemistry , catalysis
Acid‐free Friedel–Crafts chemistry: A paradox? Nucleophilicity scales, based on reactions with benzhydrylium ions, show that many π systems are more nucleophilic than aqueous or alcoholic solutions that are generally employed as solvents for S N 1 reactions. Solvolytically generated carbocations can, therefore, be trapped by donor‐substituted arenes and alkenes to form products of Friedel–Crafts‐type reactions in neutral aqueous solutions (see scheme).