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Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes |
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| Authors: | Radomir Jasiński Magda Ziółkowska Oleh M. Demchuk Agata Maziarka |
| Affiliation: | 1. Institute of Organic Chemistry and Technology, Cracow University of Technology, 31-155, Cracow, Poland 2. Faculty of Energy and Fuels, AGH University of Science and Technology, 30-059, Cracow, Poland 3. Department of Organic Chemistry, Maria Curie-Sklodowska University, 20-614, Lublin, Poland |
| Abstract: | [2+3] Cycloaddition reactions of the highly reactive (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone with (E)-2-R-nitroethenes proceed under mild conditions and yield mixtures of stereoisomeric 2-methyl-3-(3,4,5-trimethoxyphenyl)-4-nitro-5-R-isoxazolidines. The effect of regiospecificity of the cycloadditions may be accounted for by the theory of electrophilicity indexes. Stereoselectivity, however, is determined by a compilation of steric and secondary orbital effects. |
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