Hydrogen atom transfer in the photochemical isomerization of hydrazones of 1,2,4-oxadiazole derivatives.

Abstract

DFT calculations on the photoisomerization of hydrazones of 1,2,4-oxadiazole derivatives to 1,2,5-triazoles have been performed showing that the reaction occurred through the first excited singlet state. The Z isomer gave the reaction through a hydrogen atom transfer of the hydrazonic nitrogen atom to the nitrogen atom in four position on the oxadiazole ring. In this case, the isomerization was a concerted reaction. The E isomer could undergo the same reaction. However, it could not be a concerted reaction but required the presence of a ring opening intermediate.