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Synthesis and Properties of Azoles and Their Derivatives. 54. The Regioselectivity of [2+3] Cycloaddition Of C,C,N-Triphenyl- and Z-C,N-Diphenylnitrones With β- and α-Substituted Nitroethylenes in Light of Frontier Molecular Orbital Theory

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Abstract

Using quantum-chemical calculations we have carried out an analysis of frontier molecular orbital interactions in the [2+3] cycloaddition reactions of C,C,N-triphenyl- and Z-C,N-diphenylnitrones with β- and α-substituted nitroethylenes. In all of the examples studied the orbital effects lead to the formation of the corresponding 4-nitroisoxazolidines.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Technology, Cracow University of Technology, 31-155, Cracow, Poland

    R. Jasinski, A. Ciezkowska, A. Lyubimtsev & A. Baranski

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  1. R. Jasinski
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  2. A. Ciezkowska
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  3. A. Lyubimtsev
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  4. A. Baranski
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Jasinski, R., Ciezkowska, A., Lyubimtsev, A. et al. Synthesis and Properties of Azoles and Their Derivatives. 54. The Regioselectivity of [2+3] Cycloaddition Of C,C,N-Triphenyl- and Z-C,N-Diphenylnitrones With β- and α-Substituted Nitroethylenes in Light of Frontier Molecular Orbital Theory. Chemistry of Heterocyclic Compounds 40, 203–210 (2004). https://doi.org/10.1023/B:COHC.0000027893.83553.c2

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  • DOI: https://doi.org/10.1023/B:COHC.0000027893.83553.c2

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