The molecular mechanism of the rearrangement of 3-substituted 1-nitro-1H-pyrazoles into the corresponding 5-nitro-1H-pyrazoles was explored on the basis of the DFT computational study. It was found that these transformations proceed via two-step mechanism. The first step can be interpreted as [1,5]-sigmatropic NO2 shift, whereas the second step can be interpreted as [1,5]-sigmatropic proton shift.
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Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70th birthday
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1210–1212
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Jasiński, R. On the question of the molecular mechanism of N-nitropyrazole rearrangement. Chem Heterocycl Comp 56, 1210–1212 (2020). https://doi.org/10.1007/s10593-020-02799-x
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DOI: https://doi.org/10.1007/s10593-020-02799-x