Electronic and steric substituent influences on the conformational equilibria of cyclohexyl esters: The anomeric effect is not anomalous!

E Kleinpeter, F Taddei, P Wacker

Index: Kleinpeter, Erich; Taddei, Ferdinando; Wacker, Philipp Chemistry - A European Journal, 2003 , vol. 9, # 6 p. 1360 - 1368

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Citation Number: 33

Abstract

Abstract The cyclohexyl esters of a series of carboxylic acids, RCO 2 H, spanning a range of electronegativities and quotients of steric hindrance for the R substituent (R= Me, Et, iPr, tBu, CF 3, CH 2 Cl, CHCl 2, CCl 3, CH 2 Br, CHBr 2, and CBr 3) were prepared. Their conformational equilibria in CD 2 Cl 2 were examined by low-temperature 1 H NMR spectroscopy to study the axial or equatorial orientation of the ester functionality with ...