M. Jun, P. Fu
1976
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Journal
Journal of The Korean Chemical Society
Abstract
Diethyl azodicarboxylate (DAD) was reported to e任ect photochemical dehydrogenation of iso propyl alcohol and cyclohexanol,1,2 and to effect nonphotochemical oxidation of many organic compounds for the last decade. It reacts smoo thly with a variety of primary or secondary alcohols, mercaptans, anilines, and hydrazoben zenes to form aldehydes or ketones, disulfides, and azobenzenes. And also it takes place hyd rogenation to form diethyl hydrazodicarboxylate (DHAD).3,4 DAD reacts also with hydroxy amines to give nitroso compounds5 and with several 7V-monosubstituted formamides to give corresponding isocynates (isolated as urethanes).6 It is interesting to try to reveal the thermal mechanism of this reaction. At first glance, the mechanism might be sug gested "concerted," since the mechanism of the similar reaction, Diels-Alder reaction, is con certed. For instance, ethanol, phenyl hydroxyl amine, and N—substituted formamide are used below to illustrate the tentative concerted me chanism :