Semiempirical AM1 and AM1/COSMO calculations were used to examine possible pathways for the [2+3] cycloaddition of 2-nitro-1-propene to (Z)-C,N-diphenylnitrone. These reactions proceed in the gas phase through a concerted mechanism. The effect of toluene or nitromethane as a dielectric medium results in the appearance of zwitterionic intermediates on pathways leading to 3,4-cis- and 3,4-trans-4-methyl-4-nitro-2,3-diphenylisoxazolidines.
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Dedicated to the memory of Professor Genrikh Avgustovich Shvekhgeimer, our friend and teacher.
For Communication 67 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 288-299, February, 2010.
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Mikulska, M., Jasiński, R. & Barański, A. Synthesis and properties of azoles and their derivatives. 68.* [2+3] cycloaddition of 2-nitro-1-propene to (Z)-C,N-diphenylnitrone relative to AM1 and AM1/COSMO quantum-chemical calculations. Chem Heterocycl Comp 46, 232–239 (2010). https://doi.org/10.1007/s10593-010-0496-z
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DOI: https://doi.org/10.1007/s10593-010-0496-z