Abstract
A highly selective method was developed for preparation of previously unknown 1,3-dithiolanes and 1,3-dithianes by reactions of thiophene-2-carbaldehyde and its analogs with alkanedithiols under the action of trimethylchlorosilane.
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Baumann, E. and Walter, G., Ber., 1893, vol. 26, p. 1129.
Karimi, B. and Hazarkhani, H., Synthesis, 2003, vol. 16, p. 2547.
Kayzer, M.M., and Hongwei, Zhao, Gang, Chen, and Feicht, A., Arkivoc, 2002, pt. XII, no. 6, p. 47.
Grobel, B.-T. and Seebach, D., Synthesis, 1977, vol. 6, p. 357.
Zhi-Jie, Ni, Nai-Wen, Mei, Xian, Shi, Yih-Ling, Tzeng, Maw, Cherng, Wang, and Tien-Yau, Luh., J. Org. Chem., 1991, vol. 56, p. 4035.
Andenrsen, N.H., McCrae, D.A., Grotjahn, D.B., Gabhe, S.Y., Theodore, L.J., Ippolito, R.M., and Sarkar, T.K., Tetrahedron, 1981, vol. 37, p. 4069.
Ranu, B.C. and Das, A., Aust. J. Chem., 2004, vol. 57, p. 605.
Corey, E.J. and Seebach, D., Angew. Chem., 1965, 77, p. 1134.
Bulman, Page, P.C., Niel, M.B., and Prodger, J.C., Tetrahedron, 1989, vol. 45, p. 7643.
Khan, A.T., Mondal, E., Ghosh, S., and Islam, S., Eur. J. Org. Chem., 2004, p. 2002.
Perni, R.B., Synth. Commun., 1989, vol. 19, p. 2383.
Kiryanov, A.A., Seed, A.J., and Sampson, P., Tetrahedron, 2001, vol. 57, p. 5757.
Jones, T.K., Reamer, R.A., Desmond, R., and Mills, S.G., J. Am. Chem. Soc., 1990, vol. 112, p. 2998.
Elgemeie, G.H. and Sayed, S.H., Synthesis, 2001, vol. 12, p. 1747.
Yashunskii, V.G. and Kovtun, V.Yu., Usp. Khim., 1985 vol. 54, p. 126.
Poleschner, H., John, W., Kempe, G., Hoyer, E., and Fanghanel, E., Z. Chem., 1978, vol. 18, p. 345.
Jadav, J.S., Reddy, B.V.S., and Pandey, S.K., Synth. Commun., 2002, vol. 32, p. 715.
Roberts, R.M. and Cheng, C.C., J. Org. Chem., 1958, vol. 23, p. 983.
Gibson, D.T., J. Chem. Soc., 1930, vol. 1, p. 12.
Popat D. Shinde, Hanumant B. Borate, and Radhika, D. Wakharkar, Arkivoc, 2004, pt. XIV, no. 12, p. 110.
Firouzabadi, H., Iranpoor, N., and Amani, K., Synthesis, 2002, vol. 1, p. 59.
Eliel, E.L., Rao, V.S., and Riddell, F.G., J. Am. Chem. Soc., 1976, vol. 98, p. 3583.
Lambert, J.B., Majchrzak, M.W., and Daniel, Stec, III, J. Org. Chem., 1979, vol. 44, p. 4689.
Eliel, E.L. and Hutchins, R.O., J. Am. Chem. Soc., 1969, vol. 91, p. 2703.
Kumar, V. and Dev, S. Tetrahedron Lett., 1983, vol. 24, p. 1289.
Burczyk, B. and Kortylewicz, Z., Synthesis, 1982, vol. 10, p. 831.
Eliel, E.L. and Hartmann, A.A., J. Org. Chem., 1972, vol. 37, p. 505.
D’yachkova, S.G., Gusarova, N.K., Nikitina, E.A., Afonin, A.V., Deryagina, E.N., Russavskaya, N.V., and Trofimov, B.A., Phosphorous, Sulfur, and Silikon, and the Related Elements, 2004, vol. 179, p. 1355.
Grayson, D.H. and O’Donnell, S.H., Arkivoc, 2003, pt. VII, nos. 2, 4.
Papernaya, L.K., Levanova, E.P., Sukhomazova, E.N., Albanov, A.I., and Deryagina, E.N., Zh. Org. Khim., 2003, vol. 10, p. 1598.
Daudt, W.H. and Hyde, J.F., J. Am. Chem. Soc., 1952, vol. 74, p. 386.
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Original Russian Text © L.K. Papernaya, E.P. Lebanova, E.N. Sukhomasova, A.I. Albanov, E.N. Deryagina, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, no. 2, pp. 272–276.
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Papernaya, L.K., Lebanova, E.P., Sukhomasova, E.N. et al. New approach to the synthesis of cyclic 1,3-dithioacetals from thiophene-2-carbaldehydes. Russ J Org Chem 42, 256–260 (2006). https://doi.org/10.1134/S1070428002120175
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DOI: https://doi.org/10.1134/S1070428002120175