Nucleophilic addition to the double bond of 2,4,6-trinitrostyrene and transformations of adducts |
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Authors: | O. Yu. Sapozhnikov V. V. Mezhnev M. D. Dutov S. A. Shevelev |
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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: | Conditions were found under which 2,4,6-trinitrostyrene derived from 2,4,6-trinitrotoluene adds nucleophiles (thiophenol, aniline, and aliphatic amines) at the vinyl fragment to form the corresponding β-X-ethyl-2,4,6- trinitrobenzenes (X = PhS, PhNH, or R2N). In the reactions with primary aromatic amines, the initially formed adducts undergo intramolecular replacement of the nitro group followed by aromatization of the indolines that formed to the corresponding N-substituted 4,6-dinitroindoles. 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. 1022–1025, April, 2005. |
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Keywords: | 2,4,6-trinitrostyrene 2,4,6-trinitrotoluene indoles nucleophilic addition intramolecular cyclization |
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