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Type: Artigo de periódico
Title: Axial/equatorial populations in alpha-hetero-substituted cyclohexanone oximes and O-methyl oximes
Author: Ribeiro, DS
Olivato, PR
Rittner, R
Abstract: Axial equatorial populations were determined for (E)-2-X-cyclohexanone oximes and O-methyl oxime ethers in chloroform by the Eliel method [X = F, Cl, Br, OCH3, N(CH3)(2), SCH3]. A novel approach is presented, which uses H-1 NMR data from the protons bonded to C-6. The conformational proportions were also obtained from the C-4 chemical shifts, the Z-isomer spectral parameters being taken as reference for calculation. For both series, all substituents adopt preferentially the axial conformation (86-96%), but the O-methyl oxime ethers present an enhanced axial population compared with the corresponding oximes, owing to the accepted occurrence of a pi(C=NOH)/sigma(CX)* stabilizing interaction. Copyright (C) 2000 John Wiley & Sons, Ltd.
Subject: NMR
C-13 NMR
O-methyl oximes
conformational analysis
Country: Inglaterra
Editor: John Wiley & Sons Ltd
Rights: fechado
Identifier DOI: 10.1002/1097-458X(200008)38:8<627
Date Issue: 2000
Appears in Collections:Unicamp - Artigos e Outros Documentos

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