The saturated heterocyclic compounds C4H8Y, C5H10Y, and C5H10Y2 (Y = Se or Te) have been prepared by the reaction of 1,4-dibromobutane or 1,5-dibromopentane with potassium chalcogenides. The novelty of the route consists of the use of the hydrazine hydrate–KOH system for the reductive generation of potassium selenide, telluride, diselenide or ditelluride from elemental chalcogens.
Similar content being viewed by others
References
J. B. Lambert, C. E. Mixan, and D. H. Jonson, J. Am. Chem. Soc., 95, 4634 (1973).
E. Diez, A. L. Esteban, F. J. Bermejo, and M. Rico, J. Phys. Chem., 84, 3191 (1980).
A. M. Duffield, H. Budzikiewicz, and C. Djerassi, J. Am. Chem. Soc., 87, 2920 (1965).
A. L. Esteban and E. Diez, J. Org. Chem., 44, 3425 (1979).
G. Mugesh, W.-W. Du Mont, and H. Sies, Chem. Rev., 101, 2125 (2001).
J. Drabwicz and M. Mikolajczyk, Top. Curr. Chem., 208, 143 (2000).
D. H. R. Barton and W. D. Ollis (edotors), General Organic Chemistry [Russian translation], Vol. 9, Khimiya, Moscow (1985), p. 347.
E. N. Deryagina, N. V. Russavskaya, L. K. Papernaya, E. P. Levanova, E. N. Sukhomazova, and N. A. Korchevin, Izv. Akad. Nauk., Ser. Khim., 2395 (2005).
L. P. Turchaninova, N. A. Korchevin, E. N. Deryagina, B. A. Trofimov, and M. G. Voronkov, Zh. Obshch. Khim., 62, 152 (1952).
D. R. Sharafutdinova, Yu. Ya. Efremov, D. S. Ioffe, A. A. Gurlyleva, and B. Ya. Teitel'baum, Dokl. Akad. Nauk SSSR, 282, 334 (1985).
E. P. Levanova, T. I. Vakul'skaya, S. G. Shevchenko, V. A. Grabel'nykh, E. N. Sukhomazova, A. V. Elaev, A. V. Kolesnikov, L. V. Klyba, N. V. Russavskaya, A. I. Albanov, and N. A. Korchevin, Zh. Org. Khim., 44, 1446 (2008).
I. D. Sadekov, A. A. Maksimenko, and V. I. Minkin, The Chemistry of Organotellurium Compounds [in Russian], Rostov on Don University Publishing House, Rostov on Don (1983), p. 67.
E. P. Levanova, A. V. Elaev, L. V. Klyba, E. R. Zhanchipova, V. A. Grabel'nykh, E. N. Sukhomazova, A. I. Albanov, N. V. Russavskaya, and N. A. Korchevin, Zh. Obshch. Khim., 76, 2059 (2006).
J. Buckingham and S. M. Donaghy, Dictionary of Organic Compounds, Vol. 1, 5th Edition, Chapman and Hall, New York (1982).
Sigma-Aldrich Handbook of Chemical Reagents, Sigma-Aldrich, Russia (2009-2010), p. 162.
Author information
Authors and Affiliations
Corresponding author
Additional information
*Dedicated to Academician M. G. Voronkov on his 90th birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1623-1631, November, 2011.
Rights and permissions
About this article
Cite this article
Levanova, E.P., Grabel’nykh, V.A., Elaev, A.V. et al. Novel route to the synthesis of chalcogenolanes, chalcogenanes, and 1,2-dichalcogenaepanes*. Chem Heterocycl Comp 47, 1345–1352 (2012). https://doi.org/10.1007/s10593-012-0920-7
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-012-0920-7