Abstract
Using RHF/3-21G, RHF/6-31G(d, p), MP2/6-31G(d, p), B3LYP/6-31G(fd, p) approximations the structure and 13C NMR spectra of 2-alkylsubstituted cyclohexene-2-ones and 2-alkylacroleins are studied and calculated. In the series of 2-alkylcyclohexene-2-ones the effect of the substituent on a deviation from coplanarity of the C=C-C=O fragment is more expressed in comparison with 2-alkylacroleins. This deviation (5°) is not enough to explain the observed properties of 2-alkylcyclohexene-2-ones due to disturbed conjugation. The particular behavior of (R)-4-mentenone in reactions of 1,4-addition and ozonolysis is explained by a more expressed +I-effect of the alkyl substituent in α-position.
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Original Russian Text Copyright © 2007 by É. R. Latypova, R. Ya. Kharisov, I. V. Vakulin, R. F. Talipov, and G. Yu. Ishmuratov
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Translated from Zhurnal Strukturnoi Khimii, Vol. 48, No. 1, pp. 49–53, January–February, 2007.
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Latypova, É.R., Kharisov, R.Y., Vakulin, I.V. et al. Electronic effects of conjugated enones on their reactivity in transformations of ADDN type. J Struct Chem 48, 46–50 (2007). https://doi.org/10.1007/s10947-007-0007-y
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DOI: https://doi.org/10.1007/s10947-007-0007-y