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Synthesis and properties of azoles and their derivatives. 57. Unexpected results of 3-nitropropene-1 [2+3] cycloaddition to C,C,N-triphenylnitrone

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Abstract

[2+3] Cycloaddition of 3-nitropropene-1 with C,C,N-triphenylnitrone leads to a mixture of 5-nitromethyl-2,3,3-triphenylisoxazolidine and 5-methyl-4-nitro-2,3,3-triphenylisoxazolidine. The results obtained can be explained assuming that 3-nitropropene-1 isomerizes to 1-nitropropene-1 under reaction conditions.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1545–1548, October, 2006.

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Jasinski, R., Kwiatkowska, M. & Baranski, A. Synthesis and properties of azoles and their derivatives. 57. Unexpected results of 3-nitropropene-1 [2+3] cycloaddition to C,C,N-triphenylnitrone. Chem Heterocycl Compd 42, 1334–1337 (2006). https://doi.org/10.1007/s10593-006-0244-6

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  • DOI: https://doi.org/10.1007/s10593-006-0244-6

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