ON THE QUESTION OF THE MOLECULAR MECHANISM OF <i>N</i>-NITROPYRAZOLE REARRANGEMENT

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.