Intramolecular interaction between ortho-azido and azoxy groups as a new way of forming a N—N bond. Synthesis of 2-alkylbenzotriazole 1-oxides |
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Authors: | D. L. Lipilin E. E. Karslyan A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky |
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Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | Heating of 2-(alkyl-NNO-azoxy)-1-azidobenzenes in boiling benzene gave 2-alkyl-benzotriazole 1-oxides (Alk = Me, Et, Pri, and But). This first-order reaction involves an earlier unknown intramolecular interaction between the azido and azoxy groups with simultaneous release of molecular nitrogen. The cyclization rate increases in the following sequence of the alkyl groups: Me < Et < Pri < But. Complete assignment of the signals in the 1H, 13C, and 14N NMR spectra of 2-alkylbenzotriazole 1-oxides was performed. Dedicated to Corresponding Member of the Russian Academy of Sciences E. P. Serebryakov on the occasion of his 70th birthday. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 989–996, April, 2005. |
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Keywords: | azides azoxy compounds nitrogen-containing heterocycles N-oxides of heterocycles benzotriazoles cyclization 1H 13C and 14N NMR spectroscopy synthetic methods |
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