Abstract
On the basis of the reaction of sulfur with exo-halogen derivatives of ethylbenzene and styrene, new and simple methods of synthesis have been developed for 2,4-diphenylthiophene (from C6H5CHBrCH3), 2, 5-diphenylthiophene (from C6H5CCl=CH2), 2,3-dichlorothionaphthene (from C6H5CCl2CHCl2), and the previously unknown dithianaphtheno-[2,3-b;2′,3′-e]-1,4-dithiadiene (from C6H5CHClCHClBr). The latter compound is also formed by the action of sulfur on C6H5CCl2CH2Cl or C6H5CHClCHCl2 in the presence of HBr. The derivatives of thianaphthene obtained have been oxidized to the corresponding sulfones.
References
M. G. Voronkov, A. N. Pereferkovich, V. A. Pestunovich, and V. E. Udre, ZhOrKh, 3, 2211, 1967.
M. G. Voronkov and V. E. Udre, KhGS [Chemistry of Heterocyclic Compounds], 148, 683, 1965.
M. G. Voronkov and V. E. Udre, KhGS [Chemistry of Heterocyclic Compounds], 527, 1966.
E. Baumann and E. Fromm, Ber., 28, 890, 895, 1895.
E. Baumann and E. Fromm, Ber., 30, 110, 1897.
K. Meyer and W. Hohenemser, Helv. Chim. Acta, 18, 1061, 1935.
H. Westeche, Chem. Rev., 39, 219, 1946.
L. Drake, US Patent 2538722, 1951; C. A., 45, 4269, 1951.
H. Glass and E. Reid, J. Am. Chem. Soc, 51, 3428, 1929.
M. G. Voronkov and V. E. Udre, Authors' Certificate 1050577/23-4, 1966.
A. Schlesinger and D. Mowry, J. Am. Chem. Soc, 73, 2614, 1931.
O. Johnson, A. Harvey, and H. West, U. S. Patent 2758955, 1956; C. A., 50, 6027, 1956.
D. Cagniant, P. Faller, and P. Cagniant, Bull. Soc chim. France, 2410, 1961.
A. Dinesmann, C. r., 141, 201, 1905.
G. Barger, J. Chem. Soc, 95, 2194, 1909.
O. Kamm and C. Marvel, Org. Synt., 1, 23, 1937.
H. Biltz, Ann., 296, 263, 1897.
C. Glaser, Ann., 154, 155, 1870.
E. Erlenmeyer, Ber., 13, 306, 1880.
K. Auwers, Ber., 45, 2799, 1912.
E. Fromm, P. Fantl, and E. Leibsohn, Ann., 457, 275, 1937.
Author information
Authors and Affiliations
Additional information
For communication XIV see [1].
Rights and permissions
About this article
Cite this article
Voronkov, M.G., Udre, V.E. & Popova, E.P. A study of the reactions of sulfur with organic compounds. Chem Heterocycl Compd 3, 784–788 (1967). https://doi.org/10.1007/BF00474868
Issue Date:
DOI: https://doi.org/10.1007/BF00474868