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The Concept of Allopolarization. Effects of Substituents on the Reactions of Ambifunctional Anions
Author(s) -
Gompper Rudolf,
Wagner HansUlrich
Publication year - 1976
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197603211
Subject(s) - polarity (international relations) , substituent , selectivity , chemistry , computational chemistry , ion , function (biology) , stereochemistry , organic chemistry , catalysis , biochemistry , cell , evolutionary biology , biology
The chemistry of ambifunctional anions is of great importance in organic preparations. Planning of syntheses requires a set of rules correlating structure and selectivity. The concept of allopolarization permits a description of substituent effects on kinetically controlled reactions: the change in selectivity is a function of the change in polarity of the ambifunctional anions. The relative charge density P = l x /l y serves as “polarity index”; X and Y are the potential sites of reaction. An attempt is made to illustrate the utility of this principle by means of examples taken from various classes of compounds.