71200-56-1Relevant academic research and scientific papers
An Investigation into the Mechanism of Formation of Oxadiazoles and Arylidenehydrazides from the Action of Methanolic Potassium Hydroxide on 1,4-Dihydro-s-tetrazines.
Hunter, Daniel,Neilson, Douglas G.
, p. 1081 - 1086 (2007/10/02)
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.
Investigations into the Mechanism of the Action of Alkali in Methanol on 3,6-Dibenzyl-s-tetrazines and their 1,4-Dihydro-derivatives: the Role of s-Tetrazines as Hydride Acceptors and an X-Ray Determination of the Structure of 3,6-Bis(4-chlorobenzyl)-1,4-dihydro-s-tetrazine
Hunter, Daniel,Neilson, Douglas G.,Weakley, Timothy J.R.
, p. 1165 - 1170 (2007/10/02)
Evidence is presented for the mechanism of the reaction of potassium hydroxide with 3,6-dibenzyl-s-tetrazines in which some tetrazine molecules act as hydride acceptors to become dihydro-derivatives which, in turn, react with alkali in a competing reaction to form the corresponding 1,3,4-oxadiazoles.The known action of alkali on 3,6-dibenzyl-1,4-dihydro-s-tetrazines to form 1,3,4-oxadiazoles has been shown to require the presence of an oxidising agent and tetrazine can play this role.The structures of the dihydro-derivatives of s-tetrazines have been in doubt, being called 1,2- and/or 1,4-compounds almost at random, but an X-ray determination of the structure of the dihydro-derivative of 3,6-bis(4-chlorobenzyl)-s-tetrazine has shown conclusively that it exists as 1,4-dihydro-compound.
