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The predominance of axial conformers for trans ‐4‐substituted cyclohexene oxides
Author(s) -
Samoshin Vyacheslav V.,
Yartseva Irina V.,
Svyatkin Vladimir A.,
Zefirov Nikolai S.,
Palyulin Vladimir A.,
Zelenkina Olga A.,
Vereshchagina Yana A.
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199610)9:10<706::aid-poc835>3.0.co;2-2
Subject(s) - conformational isomerism , chemistry , cyclohexene , steric effects , intramolecular force , dipole , stereochemistry , computational chemistry , cis–trans isomerism , crystallography , molecule , organic chemistry , catalysis
A 1 H NMR 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 cis ‐isomers 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.