Abstract
In the gas phase at 350–410‡C allyl 2-thienyl sulfide is converted to thiophene-2-thiol, di(2-thienyl) sulfide, and 2-methylthieno[2,3-b]thiophene. In the presence of acetylene thieno[2,3-b]thiophene is formed in addition to these products. Allyl 2-thienyl selenide is converted quantitatively to 2,3-dihydro-2-methylselenopheno[2,3-b]thiophene during fractional distillation in vacuo. Thiophene, di(2-thienyl) selenide, di(2-thienyl) diselenide, thiophene-2-selenol, and 2-methylselenopheno[2,3-b]thiophene are formed in addition to these compounds in the thermolysis of allyl thienyl selenide in the gas phase. In the presence of acetylene the thermal decomposition of allyl thienyl selenide is accompanied by the formation of selenophene.
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Literature Cited
H. Kwart and R. Evans, J. Org. Chem., 31, 413 (1966).
J. Z. Mortensen, B. Hedegaard, and S.-O. Lawesson, Tetrahedron, 27, 3831 (1971).
A. V. Anisimov, V. F. Ionova, and E. A. Viktorova, Khim. Geterotsikl. Soedin., No. 2, 186 (1978).
É. N. Sukhomazova, N. V. Russavskaya, N. A. Korchevin, é. N. Deryagina, and M. G. Voronkov, Zh. Org. Khim., 25, 1506 (1989).
N. V. Russavskaya, N. A. Korchevin, é. N. Sukhomazova, é. N. Deryagina, and M. G. Voronkov, Khim. Geterotsikl. Soedin., No. 11, 1565 (1989).
L. Syper and J. Mlochowski, Synthesis, No. 5, 439 (1984).
M. G. Voronkov, é. N. Deryagina, L. K. Papernaya, é. N. Sukhomazova, N. A. Korchevin, and G. G. Efremova, Khim. Geterotsikl. Soedin., No. 12, 1614 (1986).
S. Mohmand, J. Bargon, and R. J. Waltman, J. Org. Chem., 48, 3544 (1983).
B. P. Fedorov and F. M. Stoyanovich, USSR Author's Certificate No. 165,752; Byull. Izobret., No. 20, 20 (1964).
A. Bugge, Acta Chem. Scand., 25, 27 (1971).
V. P. Litvinov and Ya. L. Gol'dfarb, Advances in Heterocyclic Chemistry, edited by A. R. Katritzky and A. J. Boulton, Vol. 19, Academic Press, New York-San Francisco-London (1976), p. 123.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1312–1316, October, 1991.
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Korchevin, N.A., Sukhomazova, É.N., Russavskaya, N.V. et al. Thermal transformations of allyl 2-thienyl sulfide and selenide. Chem Heterocycl Compd 27, 1049–1052 (1991). https://doi.org/10.1007/BF00486794
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DOI: https://doi.org/10.1007/BF00486794