Abstract
The 1Í NMR method in combination with molecular simulation was used to study conformations of Z- and E-isomers of (1R,4R)-cis-2-(4-methoxyphenyl)benzylidene-p-menthan-3-one. In solutions the Z-isomer, unlike the conformationally uniform Å-isomer, is an equilibrium mixture of chair conformers with the substantial predomination of one form with the axially oriented methyl and equatorial isopropyl groups (75—78%). The enone group is more nonplanar in the Z-isomer than in the Å-isomer. For the isopropyl fragment, the equiprobable existence of trans- and two gauche-rotamers for the Z-isomer and a substantial predomination of gauche-forms in the case of the E-isomer were established.
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Pivnenko, N.S., Vashchenko, V.V., Kutulya, L.A. et al. Conformations of Z- and E-isomers of some chiral (1R,4R)-2-arylidene-p-menthan-3-ones. Russian Chemical Bulletin 50, 1596–1604 (2001). https://doi.org/10.1023/A:1013082417885
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DOI: https://doi.org/10.1023/A:1013082417885