Abstract
An effective method is proposed for the production of the N,S-acetals of diacylketenes and acyl(alkoxycarbonyl)ketenes, based on the addition of methylene-activeβ-diketones andβ-ketoesters to alkyl and aryl thiocyanates catalyzed by Ni(2+) acetylacetonate. Methods are indicated for the synthetic utilization of diacetylketene N,S-acetals and include their conversion to ketene aminals, chelation with boron compounds, and deacylation of derivatives of monoacetylketene with methanol in the presence of Co(2+) acetate.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
R. K. Dieter, Tetrahedron,42, No. 12, 3029 (1986).
M. Yokoyama, H. Togo, and S. Kondo, Sulfur Reports,10, No. 1, 23 (1990).
D. Borrmann, Methoden der Organischen Chemie (Houben-Weyl) (E. Muller ed.), Vol. VII/4, Georg Thieme Verlag, Stuttgart (1968), p. 436.
A. Hartmann, Methoden der Organische Chemie (Houben-Weyl) (H. Hagemann ed.), Vol. EIV, Georg Thieme Verlag, Stuttgart, New York (1983), p. 968.
E. P. Kohler, Am. Chem. J.,22, 67 (1899).
K. Uehara, Y. Ohashi, and M. Tanaka, Bull. Chem. Soc. Jpn.,49, No. 5, 1447 (1976).
R. P. Eckberg, J. H. Nelson, J. W. Kenney, et al., Inorg. Chem.,16, No. 12, 3128 (1977).
M. Basato, B. Corain, A. C. Veronese, et al., J. Org. Chem.,49, No. 24, 4696 (1984).
A. S. Veronese, B. Gandolfi, B. Longato, et al., J. Mol. Catal.,54, No. 1, 73 (1989).
V. A. Dorokhov, M. F. Gordeev, Z. K. Dem'yanets, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1683 (1987).
V. A. Dorokhov, M. F. Gordeev, and V. S. Bogdanov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1431 (1988).
V. A. Dorokhov, M. F. Gordeev, Z. K. Dem'yanets, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1806 (1989).
V. A. Dorokhov and M. F. Gordeev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 941 (1988).
B. A. Ostrovskii and G. I. Koldobskii, Weak Organic Bases [in Russian], Izd. LGU, Leningrad (1990).
A. V. Iogansen, Teor. Éksp. Khim.,7, No. 3, 302 (1971).
J. Sandstrom, Topics in Stereochemistry (N. L. Allinger, E. L. Eliel, and S. H. Wilen eds.), Vol. 14, Wiley, New York (1983), p. 83.
Y. Shvo and I. Belsky, Tetrahedron,25, No. 19, 4649 (1969).
V. A. Dorokhov, M. F. Gordeev, A. V. Komkov, and V. S. Bogdanov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 401 (1990).
M. F. Gordeev, A. V. Komkov, and V. A. Dorokhov, Khim. Geterotsikl. Soedin., No. 9, 1286 (1990).
L. Gatterman and W. Haussknecht, Ber. Deutsch. Chem. Ges.,23, 738 (1890).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2600–2605, November, 1991.
Rights and permissions
About this article
Cite this article
Dorokhov, V.A., Gordeev, M.F., Shashkova, E.M. et al. Synthesis of the N,S-acetals of diacyl- and alkoxycarbonyl(acyl)ketenes with β-dicarbonyl compounds, organic thiocyanates, and nickel(2+) complexes. Russ Chem Bull 40, 2274–2279 (1991). https://doi.org/10.1007/BF00961051
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00961051