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Estimation of the Kinetic Acidity from Substrate Conformation—Stereochemical Course of the Deprotonation of Cyclohexenyl Carbamates

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  • This work was supported by the Deutsche Forschungsgemeinschaft (SFB 424) and the Fonds der Chemischen Industrie (grant for J.B.). We thank Dr. K. Bergander for temperature-dependent NMR measurements and M. Renger for her experimental assistance.

Abstract

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Get the bends: The kinetic C[BOND]H acidity of cyclohex-2-enyl carbamates is dependent on the torsion angle between the α C[BOND]H 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.

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