DOI: 10.1139/cjc-2022-0175 

A theoretical study of the reactivity of pyrazaboles with nitrogen nucleophiles (amines and pyrazoles): the ring-opening mechanism

A theoretical study of the reactivity of pyrazaboles with amines and pyrazoles has been carried out at DFT level in gas phase, toluene and water media. The reaction with amines yields two molecules of pyrazolylboranes, while the reaction with pyrazoles allows to understand the interchange of such molecules in the pyrazaboles. The reaction of three pyrazaboles with two amines [NH₃ and NMe₃] and pyrazole itself has been considered. The S_N2 and S_N1 mechanisms have been analyzed. The S_N2 reaction is more favorable than the SN1 in the absence or presence of amines.