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ON THE QUESTION OF THE MOLECULAR MECHANISM OF N-NITROPYRAZOLE REARRANGEMENT

Radomir Jasiński
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Abstract


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.


Keywords


nitropyrazole; DFT calculations; [1,5]-sigmatropic shift

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