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Relative Rates of Bromine–Magnesium Exchange Reactions in Substituted Bromobenzene Derivatives
Author(s) -
Shi Lei,
Chu Yuanyuan,
Knochel Paul,
Mayr Herbert
Publication year - 2007
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.200704100
Subject(s) - bromobenzene , bromine , halogen , chemistry , magnesium , substituent , counterintuitive , selectivity , medicinal chemistry , computational chemistry , organic chemistry , alkyl , catalysis , physics , quantum mechanics
Against expectation : How can the site of Br–Mg exchange in multiply brominated compounds be predicted? Competition experiments with different substituents X and Y (see scheme; X, Y=H, F, Cl, Br, CF 3 , CO 2 t Bu, CN) reveal a counterintuitive order of substituent effects. The aim of the study is to enable the selectivity of halogen–magnesium exchange reactions of polyfunctional compounds to be predicted.