Abstract
It was shown that the hydroxy group in β-hydroxy sulfides of the dioxothiolane series can be oxidized selectively to a carbonyl group in the presence of a sulfide group. A sequence of transformations leading to the final β-oxo sulfides was proposed and was confirmed experimentally. A new original method was developed for the production of β-oxo sulfides. Some characteristics of the synthesized compounds were studied.
REFERENCES
T. E. Bezmenova, Fiziologich. Aktiv. Veshchestva, 17, 3 (1985).
R. Kristgen, A. Olbrich, H. Rehwinkel, and W. Steglich, Liebigs Ann. Chem., 437 (1988).
J. T. Wrobel and E. Hejchman, Bull. Pol. Acad. Sci., Chem., 35, No.1–2, 21 (1987).
P. S. Jogdeo and G. V. Bhide, Steroids, 34, 729 (1979).
P. S. Jogdeo and G. V. Bhide, Steroids, 34, 619 (1979).
R. J. Strunk and R. Cmoore, US Pat. 4640927; Ref. Zh. Khim., 20O412P (1987).
C. E. Ward, US Pat. 4596595; Ref. Zh. Khim., 3O457P (1987).
J. L. Belletire and E. G. Spletzer, Synth. Commun., 13, 269 (1983).
S. N. Gaidamaka, O. A. Shantalii, and A. A. Grigor'ev, Dokl. Akad. Nauk UkrSSR, No. 3, 115 (1991).
S. N. Gaydamaka, O. A. Shantaliy, N. K. Sidorova, V. I. Slutskiy, and A. A. Grigorjev, Dokl. Akad. Nauk UkrSSR, No. 5, 132 (1994).
T. E. Bezmenova, Chemistry of Thiolene 1, 1-Dioxides [in Russian], Naukova Dumka, Kiev (1981).
G. A. Tolstikov, N. N. Novitskaya, and E. E. Shul'ts, Zh. Org. Khim., 19, 1636, (1983).
K. G. Mason, M. A. Smith, E. S. Stern, and J. H. Elvige, J. Chem. Soc. (C), 2171 (1966).
M. Prochazka, Coll. Czech. Chem. Commun., 25, 465 (1960).
K. V. Vatsuro and G. L. Mishchenko, Named Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976).
N. N. Novitskaya, B. V. Flekhter, and G. A. Tolstikov, Khim. Geterotsikl. Soedin., 1631 (1979).
S. N. Lewis and W. D. Emmens, J. Org. Chem., 31, 3572 (1966).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 974–985, July, 2005.
Rights and permissions
About this article
Cite this article
Gaydamaka, S.N., Shantaliy, O.A. & Raltshuk, I.A. Synthesis and Properties of β-Oxo Sulfides of the Dioxothiolane Series. Chem Heterocycl Compd 41, 820–830 (2005). https://doi.org/10.1007/s10593-005-0232-2
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s10593-005-0232-2