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Axial/equatorial populations in α-hetero-substituted cyclohexanone Oximes and O-methyl oximes

✍ Scribed by Douglas S. Ribeiro; Paulo R. Olivato; Roberto Rittner

Book ID: 101341273
Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 161 KB
Volume: 38
Category: Article
ISSN: 0749-1581
DOI: 10.1002/1097-458x(200008)38:8<627::aid-mrc680>3.0.co;2-m

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✦ Synopsis

Axial equatorial populations were determined for (E)-2-X-cyclohexanone oximes and O-methyl oxime ethers in chloroform by the Eliel method [X D F, Cl, Br, OCH 3 , N CH 3 2 , SCH 3 ]. A novel approach is presented, which uses 1 H 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 CDNOH / Ł CX stabilizing interaction.

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