

ON THE QUESTION OF THE MOLECULAR MECHANISM OF N-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.
Keywords
nitropyrazole; DFT calculations; [1,5]-sigmatropic shift
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv