Tetrahedron

Synthesis and NMR spectroscopic conformational analysis of esters of 4-hydroxy-cyclohexanone—the more polar the molecule the more stable the axial conformer

E Kleinpeter, M Heydenreich, A Koch, T Linker

文献索引：Kleinpeter, Erich; Heydenreich, Matthias; Koch, Andreas; Linker, Torsten Tetrahedron, 2012 , vol. 68, # 10 p. 2363 - 2373

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被引用次数: 8

摘要

The esters of 4-hydroxy-cyclohexanone and a series of carboxylic acids R–COOH with R of different electronic and steric influence (R= Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, sec-Bu, t-Bu, CF3, CH2Cl, CHCl2, CCl3, CH2Br, CHBr2, and CBr3) were synthesized and the conformational equilibria studied by 1H and 13C NMR spectroscopy at 103 K and at 295 K, respectively. The geometry of optimized structures of the axial/equatorial chair conformers was ...