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Axial/equatorial populations in ?-hetero-substituted cyclohexanone Oximes andO-methyl oximes

2000; Wiley; Volume: 38; Issue: 8 Linguagem: Inglês

10.1002/1097-458x(200008)38

1097-458X

Douglas S. Ribeiro, Paulo R. Olivato, Roberto Rittner,

Crystallography and molecular interactions

Magnetic Resonance in ChemistryVolume 38, Issue 8 p. 627-638 Research Article Axial/equatorial populations in α-hetero-substituted cyclohexanone Oximes and O-methyl oximes Douglas S. Ribeiro, Douglas S. Ribeiro Instituto de Química, Universidade de São Paulo, Caixa Postal 26.077, 05599-970 São Paulo– S. P., BrazilSearch for more papers by this authorPaulo R. Olivato, Paulo R. Olivato Instituto de Química, Universidade de São Paulo, Caixa Postal 26.077, 05599-970 São Paulo– S. P., BrazilSearch for more papers by this authorRoberto Rittner, Corresponding Author Roberto Rittner [email protected] Instituto de Química, Universidade Estadual de Campinas, Caixa Postal 6154, 13081-970 Campinas– S. P., BrazilInstituto de Química, UNICAMP, Caixa Postal 6154, 13083-970 Campinas– S. P., Brazil===Search for more papers by this author Douglas S. Ribeiro, Douglas S. Ribeiro Instituto de Química, Universidade de São Paulo, Caixa Postal 26.077, 05599-970 São Paulo– S. P., BrazilSearch for more papers by this authorPaulo R. Olivato, Paulo R. Olivato Instituto de Química, Universidade de São Paulo, Caixa Postal 26.077, 05599-970 São Paulo– S. P., BrazilSearch for more papers by this authorRoberto Rittner, Corresponding Author Roberto Rittner [email protected] Instituto de Química, Universidade Estadual de Campinas, Caixa Postal 6154, 13081-970 Campinas– S. P., BrazilInstituto de Química, UNICAMP, Caixa Postal 6154, 13083-970 Campinas– S. P., Brazil===Search for more papers by this author First published: 07 July 2000 https://doi.org/10.1002/1097-458X(200008)38:8 3.0.CO;2-MCitations: 13AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL 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. REFERENCES 1Allinger NL, Allinger J, Freiberg LA, Czaja RF, Lebel NA. J. Am. Chem. Soc. 1960; 82: 5876. 2Eliel EL, Allinger NL, Angyal SJ, Morrison CA. Conformational Analysis. Interscience: New York, 1965; 112– 115, 460– 469. 3Basso EA, Kaiser C, Rittner R, Lambert JB. J. Org. Chem. 1993; 58: 7865. 4Saitô H, Teresawa I, Ohno M, Nukada K. J. Am. Chem. Soc. 1969; 91: 6696. 5Denmark SE, Dappen MS. J. Org. Chem. 1984; 49: 798. 6Denmark SE, Dappen MS, Sear NL, Jakobs RT. J. Am. Chem. 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