Conclusions
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1.
The successive treatment at -70° of either 3,4-dibromothiophene or 3,4-dibromoselenophene with one equivalent of n-butyllithium, dimethylformamide and a second equivalent of n-butyllithium results in the exchange of one bromine atom and the adjacent hydrogen atom in theα-position, with a retention of the second bromine atom in the heterocycle.
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2.
A number ofβ-monobromo-substituted thieno[2,3-b]thiophene and selenopheno[2,3-b]thiophene derivatives was obtained.
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Literature cited
V. S. Bogdanov, V. P. Litvinov, J. L. Goldfarb, N. N. Petukhova, and E. G. Ostapenko, J. Prakt. Chem. (in press).
A. Biederman and P. Jacobson, Ber.,19, 2444 (1886).
G. Capelle, Bull. Soc. Chim. France [4],3, 154 (1908).
F. Challenger and J. B. Harrison, J. Inst. Petrol. Techn.,21, 135 (1935).
J. Bruce, F. Challenger, H. B. Gibson, and W. E. Allenby, J. Inst. Petrol.,34, 226 (1948).
A. Bugge, Acta Chem. Scand.,23, 2704 (1969).
S. Gronowltz, Advan. Heterocycl. Chem.,1, 75 (1963).
V. P. Litvinov, J. L. Goldfarb, V. S. Bogdanov, I. P. Konjaeva, and A. N. Sukiasjan, J. Prakt. Chem.,315, 850 (1973).
V. P. Litvinov and G. Frénkl, Izv. Akad. Nauk SSSR, Ser. Khim., 1828 (1968).
P. Moses and S. Gronowitz, ArkivKemi,18, 119 (1961).
S. Gronowitz, P. Moses, A.-B. Hörnfeldt, and R. Hakansson, Arkiv Kemi,17, 165 (1961).
M. Robba, R. C. Moreau, and B. Roques, Compt. Rend.,259, 3568 (1964).
S. Gronowitz, A. Biezais, and B. Mathiasson, Arkiv Kemi,21, 265 (1963).
S. O. Lawesson, Arkiv Kemi,11, 325 (1957).
A. Bugge, B. Gestblom, and O. Hartmann, Acta Chem. Scand.,24, 105 (1970).
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See [1] for Communication 26.
Translated from Izvestiya Akademii.Nauk SSSR, Seriya Khimichesaya, No. 7, pp. 1570–1574, July, 1974.
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Gol'dfarb, Y.L., Konyaeva, I.P. & Litvinov, V.P. Condensed heteroaromatic systems that contain a thiophene ring. Russ Chem Bull 23, 1488–1492 (1974). https://doi.org/10.1007/BF00929659
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DOI: https://doi.org/10.1007/BF00929659