Bromination of 1-(4-nitrophenyl)-2-formylpyrrole |
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Authors: | É Baum L I Belen'kii V G Kul'nevich T E Goldovskaya |
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Institution: | (1) Krasnodar Polytechnic Institute, 350006 Krasnodar;(2) N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913 Moscow |
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Abstract: | Depending on the amount of bromine, the bromination of 1-(4-nitrophenyl)-2-formylpyrrole with bromine in chloroform without a catalyst gives 5-bromo and 4,5-dibromo derivatives. 4-Bromo-1-(4-nitrophenyl)-2-formylpyrrole is formed in the presence of excess AlC13, while a mixture of 3,4- and 4,5-dibromo derivatives with preponderance of the latter is formed with excess bromine. The results are compared with the literature data on the bromination of 2-formylpyrrole, 2-formylfuran, and 2-formylthiophene and are interpreted with allowance for the electronacceptor effect of the p-nitrophenyl substituent attached to the nitrogen atom of the pyrrole ring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 662–665, May, 1982. |
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