caa a22 4500 463238834 CHVBK 20180405153306.0 cr unu---uuuuu 170326e20070101xx s 000 0 eng 10.1007/s10947-007-0007-y doi (NATIONALLICENCE)springer-10.1007/s10947-007-0007-y Electronic effects of conjugated enones on their reactivity in transformations of ADDN type [Elektronische Daten] [É. Latypova, R. Kharisov, I. Vakulin, R. Talipov, G. Ishmuratov] 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. Springer Science+Business Media, Inc., 2007 (R)-4-mentenone nationallicence 2-alkylsubstituted cyclohexene-2-ones and alkylacroleins nationallicence conformation analysis nationallicence ab initio calculations nationallicence Latypova É. Bashkir State University, Ufa aut Kharisov R. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, Russia aut Vakulin I. Bashkir State University, Ufa aut Talipov R. Bashkir State University, Ufa aut Ishmuratov G. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, Russia aut Journal of Structural Chemistry Kluwer Academic Publishers-Consultants Bureau 48/1(2007-01-01), 46-50 0022-4766 48:1<46 2007 48 10947 https://doi.org/10.1007/s10947-007-0007-y text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10947-007-0007-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Latypova É. Bashkir State University, Ufa aut NATIONALLICENCE 700 1- Kharisov R. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, Russia aut NATIONALLICENCE 700 1- Vakulin I. Bashkir State University, Ufa aut NATIONALLICENCE 700 1- Talipov R. Bashkir State University, Ufa aut NATIONALLICENCE 700 1- Ishmuratov G. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, Russia aut NATIONALLICENCE 773 0- Journal of Structural Chemistry Kluwer Academic Publishers-Consultants Bureau 48/1(2007-01-01), 46-50 0022-4766 48:1<46 2007 48 10947 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer