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Estimation of the Kinetic Acidity from Substrate Conformation—Stereochemical Course of the Deprotonation of Cyclohexenyl Carbamates
Author(s) -
Becker Jochen,
Grimme Stefan,
Fröhlich Roland,
Hoppe Dieter
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.200603347
Subject(s) - deprotonation , chemistry , kinetic energy , substrate (aquarium) , double bond , computational chemistry , stereochemistry , medicinal chemistry , organic chemistry , physics , geology , ion , oceanography , quantum mechanics
Get the bends : The kinetic CH acidity of cyclohex‐2‐enyl carbamates is dependent on the torsion angle between the α CH bond and the π system of the adjacent double bond. A deprotonation study and DFT calculations of the activation energies for lithiation show that the ease of deprotonation is predictable from a conformational analysis of the substrates. Furthermore, the stereochemical course of substitution reactions was determined.