Zusammenfassung
α-Substituierte β-Acylvinylphosphonate3 mitE-Konfiguration [R 2CO-CH=C(R 1)-P(O)(OR′)2], werden in guten Ausbeuten durchWittig-Reaktion von Acylphosphonsäureestern1 [R 1CO-P(O)(OR′)2,R 1=Alkyl oder Aryl] mit (2-Oxoalkyliden)triphenylphosphoranen2 [R 2CO-CH=PPh 3,R 2=Alkyl, O-Alkyl oder CH2 X (X=Br, OMe, CO2 Et)] erhalten.
Abstract
α-Substituted dialkyl (E)-β-acylvinylphosphonates [R 2CO-CH=C(R 1)-P(O)(OR′)2,3], are easily obtained in good yields byWittig-reaction of dialkyl acylphosphonates1 [R 1CO-P(O)(OR′)2,R 1=alkyl or aryl) with 2-oxoalkylidene triphenylphosphoranes2 [R 2CO-CH=PPh 3,R 2=alkyl, O-alkyl and CH2 X (X=Br, OMe, CO2 Et)].
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Literatur
Hammerschmidt F.,Zbiral E., Liebigs Ann. Chem.1979, 492.
Öhler E., Zbiral E., El-Badawi M., Tetrahedron. Lett.24, 5599 (1983).
Öhler E., Zbiral E., Monatsh. Chem.115, 493 (1984).
Öhler E., Zbiral E., Monatsh. Chem.115, 629 (1984).
Öhler E., Zbiral E., El-Badawi M., Chem. Ber.117, 3034 (1984).
Shin Ch., Yonezawa Y., Katayama K., Yoshimura Y., Bull. Chem. Soc. Jpn.46, 1727 (1973).
Kirillova K. M., Kulitin V. A., Zh. Obshch. Khim.35, 1146 (1965); Chem. Abstr.63, 11418 h (1965).
Kuklitin V. A.,Samitov Yu. Yu.,Kirllova K. M., Izv. Akad. Nauk. SSSR, Ser. Khim.1967, 356; Chem. Abstr.67, 21361 s (1967).
Pudovik A. N., Zimin M. G., Sobanov A. A., Vinogradov, L. I., Samitov, Yu. Yu., Zh. Obshch. Khim.42, 2167 (1972); Chem. Abstr.78, 72306 u (1973).
Pfeiffer G.,Guillemonat A.,Buono G., Bull. Soc. Chim. Fr.1969, 946.
Nurtdinov S. Kh.,Savran V. J.,Zykova T. V.,Salakhutdinov R. A., Khimija i Praktich. Primenenie Kremnii i Fosfororganich. Soedin,1979, 121; Chem. Abstr.93, 114 630 f (1980).
Kojima M.,Yamashita M.,Yoshida H.,Ogata T., Synthesis1979, 147;
Yamashita M., Kojima M., Yoshida H., Ogata T., Inokawa S., Bull. Chem. Soc. Jpn.53, 1625 (1980).
Sekine M.,Kume A.,Nakajima M.,Hata T., Chem. Lett.1981, 1087, und dort zitierte Literatur.
Hammerschmidt F., Schneyder E., Zbiral E., Chem. Ber.113, 3891 (1980), und dort zitierte Literatur.
le Corré M., C.R. Acad. Sci. Ser. C.273, 81 (1971);
le Corré M., Bull. Soc. Chim. Fr.1974, 1951.
Pietrusiewicz K. M., Monkiewicz J., J. Org. Chem.48, 788 (1983);
Serratosa F., Sole E., An. Real. Soc. Espan. Fis. Quim. (Madrid), Ser. B.62, 431 (1966); Chem. Abstr.66, 2623 g (1967).
Mavel G., in: Annual Report on NMR-Spectroscopy, Bd. 5 B, S. 49 (Mooney E. F., ed.). London: Academic Press. 1973.
Lit.3 und dort zitierte Literatur.
Sasse K., in: Methoden der organischen Chemie (Houben-Weyl-Müller), 4. Aufl., Bd. 12/1, S. 453. Stuttgart: G. Thieme. 1963.
Costisella B., Keitel J., Gross H., Tetrahedron37, 1227 (1981).
Ramirez F., Dershowitz S., J. Org. Chem.22, 41 (1957).
Sucrow W., Schubert B., Richter W., Slopianka M., Chem. Ber.104, 3689 (1971).
Zbiral E., Fenz L., Monatsh. Chem.96, 1983 (1965).
Harris R. L. N., McFadden H. G., Austr. J. Chem.37, 417 (1984).
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Öhler, E., El-Badawi, M. & Zbiral, E. Ein einfacher Weg zu α-substituierten (E)-3-Oxo-1-alkenylphosphonsäureestern. Monatsh Chem 116, 77–86 (1985). https://doi.org/10.1007/BF00798281
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DOI: https://doi.org/10.1007/BF00798281