Abstract
In the presence of an equivalent amount of sulfuric acid 3-methyl-2,3-epoxysulfolane reacts with sodium thiocyanate with primary opening of the oxy ring at the C(3)-O bond to give, as the principal product, 5-methyl-3-oxo-2-oxa-4,8-dithiabicyclo[3.3.0]octane 8,8-dioxide.
Similar content being viewed by others
Literature cited
L. A. Mukhamedova, L. I. Kursheva, and M. V. Konoplev, Khim. Geterotsikl. Soedin., No. 10, 1333 (1982).
N. N. Mel'nikov and N. D. Sukhareva, Reactions and Methods for the Investigation of Organic Compounds [in Russian], Vol. 8, Goskhimizdat, Moscow (1959), p. 12.
A. A. Akhrem, Z. I. Istomina, A. M. Turuta, and G. A. Kogan, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 90 (1973).
I. G. Tishchenko, P. M. Malashko, and O. N. Bubel', in: The Synthesis of Organic Compounds [in Russian], Nauka i Tekhnika, Minsk (1970), p. 14.
A. A. Krauze, Z. A. Bomika, Yu. É. Pelcher, I. B. Mazheika, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 4, 508 (1982).
Houben-Weyl, Methods of Organic Chemistry. Analytical Methods [Russian translation], Vol. 11, Goskhimizdat, Moscow (1963), p. 584.
L. Bellamy, Infrared Spectra of Complex Molecules, Methuen, London (1958).
L. A. Mukhamedova, L. I. Kursheva, and N. P. Anoshina, Zh. Org. Khim., 11, 2450 (1975).
L. A. Mukhamedova and L. I. Kursheva, Khim. Geterotsikl. Soedin., No. 5, 613 (1979).
J. Mathieu and J. Weill-Raynal, Introduction of an a-Functional Carbon Chain and Special Condensation Reactions, PSG Publ. (1980).
E. E. Van Tamelen, J. Am. Chem. Soc., 73, 3444 (1951).
A. V. Kamernitskii and A. M. Turuta, Usp. Khim., 51, 1516 (1982).
A. A. Akhrem, I. V. Vesela, and A. V. Kamernitskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 416 (1974).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 331–335, March, 1985.
Rights and permissions
About this article
Cite this article
Mukhamedova, L.A., Kursheva, L.I., Enikeev, K.M. et al. Formation of bicyclic compounds in the reaction of 3-methyl-2,3-epoxysulfolane with thiocyanic acid. Chem Heterocycl Compd 21, 273–276 (1985). https://doi.org/10.1007/BF00506663
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00506663