501664-67-1Relevant academic research and scientific papers
A new cyclization involving the diazonium and ortho-(tert-butyl)-NNO-azoxy groups - Synthesis of 1,2,3,4-benzotetrazine 1-oxides
Lipilin, Dmitry L.,Smirnov, Oleg Yu.,Churakov, Aleksandr M.,Strelenko, Yuri A.,Ioffe, Sema L.,Tartakovsky, Vladimir A.
, p. 3435 - 3446 (2007/10/03)
The synthesis of 1,2,3,4-benzotetrazine 1-oxides (BTOs) is described. Bromo-BTOs 4b-d were prepared by the intramolecular cyclization of diazonium salts bearing an ortho-(tert-butyl)-NNO-azoxy group. BTOs bearing electron-releasing substituents were obtained by nucleophilic displacements of bromine in 4b-d. The formation of the BTO cyclic system involves the intermediate 2-(tert-butyl)-1,2,3,4-benzotetrazinium 4-oxides, which arise from an N,N-[1,21-shift of the tert-butyl group. Decomposition of BTOs involves opening of the tetrazine ring to afford ortho-azidonitroso derivatives, followed by their cyclization with the evolution of the N2 molecule to give benzofurazans. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
