An investigation into the mechanism of formation of oxadiazoles and arylidenehydrazides from the action of methanolic potassium hydroxide on 1,4-dihydro-s-tetrazines.

Abstract

3,6-Diaryl- and 3,6-dibenzyl-1,4-dihydro-s-tetrazines have been shown to be inert to methanolic alkali under nitrogen. Oxadiazoles derived from these substances by the action of alkali in methanol in air result from alkali attack on the tetrazines themselves and not on the reduced derivatives as previously believed. 1,4-Dihydro-3,6-bis(α-hydroxybenzyl)-s-tetrazine is likewise stable to alkali under nitrogen but on exposure to air yields the benzylidene derivative of mandelohydrazide. Mechanisms are here proposed for the formation of the oxadiazoles and hydrazides.