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Type: Artigo de periódico
Title: Axial/equatorial Populations In α-hetero-substituted Cyclohexanone Oximes And O-methyl Oximes
Author: Ribeiro D.S.
Olivato P.R.
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 1H 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 πC=NOH//σ*CX stabilizing interaction. Copyright © 2000 John Wiley & Sons, Ltd.
Rights: fechado
Identifier DOI: 
Date Issue: 2000
Appears in Collections:Unicamp - Artigos e Outros Documentos

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