Abstract
The title compounds3 can be prepared either from the iodonium-ylides1 or from the chlorocompounds4. On treatment with hydrochloric acid the thiophanium-ylides3 C undergo ring cleavage to the chlorobutylsulfides5, also formed from4 and thiophane. The dimethylsulfonium-ylide8 is derived from activatedDMSO and7 b. TheOrtoleva-King reaction is discussed as an alternative method for preparing pyridiniumylides.
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Literatur
III. Mitteilung:Kappe Th., Hariri M., Pongratz E., Monatsh. Chem.112, 1211 (1981).
Johnson A. W., in: Organic Chemistry (Blomquist, Hrsg.), 1. Aufl., Bd. 7 (Ylid Chemistry). New York: Academic Press. 1966.
Zugravescu I., Petrovanu M., N-Ylid Chemistry. New York: McGraw-Hill. 1976.
Sadekov I. D., Minkin V. I., Semenov V. V., Shevlev S. A., Usp. Khim.50, 813 (1981);Belkin Yu. V., Polezhaeva N. A., ibid., 909 (1981).
Trost B. M., Melvin L. S., jr., in: Organic Chemistry (Blomquist, Wassermann, Hrsg.), 1. Aufl., Bd. 31 (Sulfur Ylides). New York: Academic Press. 1975.
Neiland O. Ya.,Kampare R. B.,Prikule D. Y.,Liepin E. E., Khim. Geterotsikl. Soedin.1979, 379.
Neiland O. Ya.,Krauze A. A., ibid.1980, 1637;Yousif M. M.,Saeki S.,Hamana M., Heterocycles15, 1083 (1981).
Neiland O. Ya.,Adamson B. Ya., Khim. Geterotsikl. Soedin.1979, 379.
Schwarz A.,Uray G.,Junek H., Liebigs Ann. Chem.1980, 1919;Zaslona A. T.,Hall C. D., J. Chem. Soc., Perkin Trans. I1981, 3059.
Connor D. T., Sorenson R. J., J. Heterocycl. Chem.18, 587 (1981).
Simonov V. D., Chernova L. N., Akhmerova S. G., Yasman Ya. B., Zh. Org. Khim.16, 2313 (1980);Agarwal N. L., Schäfer W., J. Org. Chem.45, 5139 (1980);Gewald K., International Congress of Heterocyclic Chem., Graz 1981, Abstract Book S. 11; Lectures in Heterocyclic Chem., Vol. 6, S. 121 (1982).
Gillespie R. J.,Murray-Rust J.,Murray-Rust P.,Porter E. A., J. C. S., Chem. Commun.1978, 83;Tamura Y.,Bayomi S. M. M.,Takebe Y.,Mukai C.,Ikeda M.,Murase M.,Kise M., 8th International Congress of Heterocyclic Chemistry (Graz, 1981, Abstract Book, S. 293);Tamura Y.,Takebe Y.,Mukai C.,Ikeda M., Heterocycles15, 857 (1981).
Prikule D. E., Neiland O. Ya., Zh. Org. Khim.17, 2119 (1981).
Schindler G.,Kappe Th., Synthesis1977, 243.
Kappe Th., Korbuly G., Stadlbauer W., Chem. Ber.111, 3857 (1978) und dort zitierte Literatur.
Krauch H., Kunz W., Reaktionen der Organischen Chemie, 3. Aufl., S. 433. Heidelberg: Dr. A. Hüthig Verlag. 1966;Ortoleva G., Gazz. chim. ital.29 I, 503 (1899); ibid.30 I, 509 (1900);King L. C., J. Amer. Chem. Soc.66, 894 und 1612 (1944);King L. C., McWhriter M., ibid.68, 717 (1946);Hamer J., Macaluso A., Chem. Rev.64, 481 (1964).
Kappe Th., Pongratz E., Österr. Chem. Z.82 (9), 243 (1981). (Vortrags-Zusammenfassung.)
Zollner H., unveröffentlicht.
Wolfbeis O. S., Uray G., Monatsh. Chem.109, 123 (1978).
Martin D., Niclas H., Chem. Ber.102, 31 (1969);Cook A., Moffatt J., J. Amer. Chem. Soc.90, 740 (1968).Seitz G., Chem. Ber.101, 585 (1968).
Mancuso A. J.,Swern D., Synthesis1981, 165.
Hochrainer A., Wessely F., Monatsh. Chem.97, 1 und 823 (1966);Hochrainer A., Wessely F., Tetrahedron Lett.1965, 721.
Schank K.,Schuhknecht C., Synthesis1978, 678.
Gompper R., Euchner H., Chem. Ber.99, 527 (1966).
Wittmann H., Orlinger F., Ziegler E., Monatsh. Chem.96, 1200 (1965).
Mentzer C.,Meunier P., Bull. Soc. Chim. Fr.1943, 379;Boetius M.,Carstens E.,Meyer C., Dtsch. Pat. (DDR) 13,870, 21. Sept. 1957; [Chem. Abstr.53, P11415f (1959)];Trivedi J. M.,Mehta C. M., J. Ind. Chem. Soc.1973, 231;Oels R.,Storer R.,Young D. W., J. C. S., Perkin Trans. I1977, 2549.
Ashley J. N.,Perkin W. H.,jr.,Robinson R., J. Chem. Soc.1930, 382.
Vilsmaier E., Tröger W., Angew. Chem.91, 860 (1979);Vilsmaier E., Tröger W., Haag G., Chem. Ber.114, 67 (1981) und dort zit. Literatur.
Grier N., Strelitz R., J. Pharm. Sci.65, 616 (1976).
Covello M., Abignente E., Dini A., Ann. Chim. (Rom)55, 239 (1965).
Ziegler E., Salvador R., Kappe Th., Monatsh. Chem.94, 941 (1963).
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Kappe, T., Korbuly, G. & Pongratz, E. Ylide von Heterocyclen, IV. Sulfonium- und Pyridinium-Ylide des Cumarins und des 2-Chinolons. Monatsh Chem 114, 303–315 (1983). https://doi.org/10.1007/BF00798953
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DOI: https://doi.org/10.1007/BF00798953