Crystal structure and DFT studies of 4-methyl-N-(1-phenylethyl)-N′-(1-phenylethylidene)benzenesulfono-hydrazide: evidence of a carbene insertion in the formation of acetophenone azine from acetophenone p-toluensulfonylhydrazone

The crystal structure of 4-Methyl-N-(1-phenylethyl)-N′-(1-phenylethylidene) benzene sulfonohydrazide is disclosed, which is obtained from direct reaction between acetophenone tosylhydrazone and potassium tert-butoxide. Reaction mechanisms and the corresponding energy barriers were assessed through DFT calculations at the B3LYP/6-31G(d,p) level of theory and showed that this compound plays an important role as an intermediate in the formation of acetophenone azine from acetophenone p-toluensulfonylhydrazone through a carbene insertion on this last compound.