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Journal of Structural Chemistry

, Volume 48, Issue 1, pp 46–50 | Cite as

Electronic effects of conjugated enones on their reactivity in transformations of ADDN type

  • É. R. Latypova
  • R. Ya. Kharisov
  • I. V. Vakulin
  • R. F. Talipov
  • G. Yu. Ishmuratov
Article

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.

Keywords

(R)-4-mentenone 2-alkylsubstituted cyclohexene-2-ones and alkylacroleins conformation analysis ab initio calculations 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • É. R. Latypova
    • 1
  • R. Ya. Kharisov
    • 2
  • I. V. Vakulin
    • 1
  • R. F. Talipov
    • 1
  • G. Yu. Ishmuratov
    • 2
  1. 1.Bashkir State UniversityUfa
  2. 2.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesRussia

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