Abstract
The electrophilic trichloromethylation of 3-chloro-, 3-bromo-, and 3,4-dibromothiophene was studied. It is shown that reaction is directed towards position 2, accompanied by frequent formation of the corresponding substituted di-(2-thienyl)dichloromethane. Trichloromethylation of β-bromothiophenes is complicated by exchange of chlorine for bromine under the reaction conditions.
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L. I. Belen'kii, G. P. Gromova, and M. M. Krayushkin, Gazz. Chim. Ital., 120, 365 (1990).
S. Conde, G. Corral, R. Madroneso, and A. Sanches, Synthesis, No. 6, 412 (1990).
L. I. Belen'kii, G. P. Gromova, and Ya. L. Gold'farb, Khim. Geterotsikl. Soedin., No. 11, 1464 (1975).
B. Roques, M.-Cl. Zaluski, and M. Dutheil, Bull. Soc. Chim. France, No. 1, 238 (1971).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc., Perkin Trans. I, No. 16, 1766 (1973).
B.-P. Roques, M.-Cl. Fournie-Zaluski, and R. Oberlin, Bull. Soc. Chim. France, No. 9–10, Pt. 2, 2334 (1975).
S. Gronowitz, Arkiv Kemi, 16, 267 (1960).
D. J. Chadwick, J. Chambers, G. D. Meakins, and R. L. Snowden, J. Chem. Soc., Perkin Trans. I, No. 16, 1766 (1973).
B. Decroix, J. Morel, C. Paulmier, and P. Pastour, Bull. Soc. Chim. France, No. 5, 1848 (1972).
S.-O. Lawesson, Arkiv Kemi, 11, 373 (1957).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1046–1048, August, 1993.
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Gromova, G.P., Belen'kii, L.I. & Krayushkin, M.M. Electrophilic trichloromethylation of some halogenated thiophenes. Chem Heterocycl Compd 29, 889–891 (1993). https://doi.org/10.1007/BF00534264
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DOI: https://doi.org/10.1007/BF00534264