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The predominance of axial conformers for trans-4-substituted cyclohexene oxides

โœ Scribed by Vyacheslav V. Samoshin; Irina V. Yartseva; Vladimir A. Svyatkin; Nikolai S. Zefirov; Vladimir A. Palyulin; Olga A. Zelenkina; Yana A. Vereshchagina

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
332 KB
Volume
9
Category
Article
ISSN
0894-3230

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โœฆ Synopsis

A 'H N M R conformational study of cis-and trans-4-substituted cyclohexene oxides revealed an increased predominance, as compared with the parent 4-substituted cyclohexenes, of the equatorial conformer for cisisomers and a preference of the axial conformer for trans-isomers. These conformational shifts can be rationalized in terms of intramolecular dipole-dipole and/or steric interactions. However, molecular mechanics calculations failed to reproduce the relative stability of the axial conformer in trans-4-substituted cyclohexene oxides.

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