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Darstellung, Struktur und Reaktionsfähigkeit einiger Metallderivate des Äthoxycarbonylmethan-phosphonsäurediäthylesters

Synthesis, structure and reactivity of some metal-derivatives of diethyl ethoxycarbonylmethane phosphonate

  • Anorganische, Strucktur- und Physikalische Chemie
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Abstract

Treating of the diethyl ester of ethoxycarbonylmethanephosphonic acid (CMPD) with metallic Li in benzene, metallic Ca in liquid ammonia and isopropylmagnesium bromide or propylmagnesium chloride in ether the corresponding metalderivatives of the ester have been obtained. Their structure has been established by means of IR- and1H-NMR-spectra. With benzyl chloride and acyl chlorides they give the corresponding C-derivatives ofCMPD. With carbonyl compounds PO-activated formation of olefines takes place giving ethyl esters of the corresponding β-substituted unsaturated acids, and diethyl phosphate.

Zusammenfassung

Durch Behandlung von Äthoxycarbonylmethan-phosphonsäure-diäthylester (CMPD) mit metallischem Li in Benzol, metall. Ca in flüssigem NH3, Isopropylmagnesiumbromid und Propylmagnesiumchlorid in Äther wurden die jeweiligen Metallderivate desCMPD isoliert. Ihre Struktur wurde IR-und1H-NMR-spektralanalytisch nachgewiesen. Mit Benzylchlorid und Acylchloriden liefern sie die entsprechenden C-Derivate vonCMPD. Mit Carbonylverbindungen läuft die PO-aktivierte Olefinierung zum Äthylester der jeweiligen β-substituierten Propensäuren und Diäthylphosphat ab.

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Literatur

  1. A. Arbuzov undA. Razumov, J. russ. fisiko-khim. Obshch.61, 623 (1929); Chem. Abstr.23, 4444 (1929).

    Google Scholar 

  2. A. Arbuzov undA. Razumov, J. obshch. Khim.4, 834 (1934); Chem. Abstr.29, 2145 (1935).

    Google Scholar 

  3. V. Chavane, Ann. Chim. [12]4, 352 (1949).

    Google Scholar 

  4. G. Kosolapoff undJ. Powell, J. Amer. Chem. Soc.72, 4198 (1950).

    Google Scholar 

  5. A. Pudovik, L. Scelkina undL. Basirova, J. obshch. Khim.27, 2367 (1957); Chem. Abstr.52, 7134 (1958).

    Google Scholar 

  6. N. Kreutzkamp, Chem. Ber.88, 195 (1955).

    Google Scholar 

  7. A. Pudovik undN. Lebedeva, J. obshch. Khim.22, 2128 (1952); Chem. Abstr.48, 564 (1954).

    Google Scholar 

  8. B. Fiszer undJ. Michalski, Roczn. chem.28, 185, (1954).

    Google Scholar 

  9. M. Kirilov undJ. Petrova, Mh. Chem.99, 148 (1968).

    Google Scholar 

  10. W. Wadsworth, Jr., undW. Emmons, J. Amer. Chem. Soc.83, 1733 (1961).

    Google Scholar 

  11. Takahashi Hidetaka, Fujiwara Kazuyoshi undOhta Masaki, Bull. Chem. Soc. Japan35, 1498 (1962).

    Google Scholar 

  12. M. Kirilov undG. Petrov, Chem. Ber.100, 3139 (1967).

    Google Scholar 

  13. G. Petrov undM. Kirilov, Mh. Chem.99, 1923 (1968).

    Google Scholar 

  14. M. Gaudemar, Bull. Soc. Chim. (France)10, 3113 (1966).

    Google Scholar 

  15. G. Wittig undH. Laib, Ann. Chem.580, 57 (1953).

    Google Scholar 

  16. L. Horner, H. Hoffmann undH. Wippel, Chem. Ber.91, 61 (1958).

    Google Scholar 

  17. A. Arbuzov undG. Kamaj, J. russ. fisiko-khim. Obshch.61, 619 (1929); Chem. Abstr.23, 4443 (1929).

    Google Scholar 

  18. A. D. F. Toy, J. Amer. Chem. Soc.70, 3882 (1948);G. Kosolapoff, Organophosphorus Compounds, S. 253. London-New York: Chapman. 1958.

    Google Scholar 

  19. K. Auwers undF. Eisenlohr, J. prakt. Chem.84, 84, (1911).

    Google Scholar 

  20. G. Kon undR. Linstead, J. Chem. Soc. [London]127, 624 (1925).

    Google Scholar 

  21. W. Schlenk undE. Bergmann, Ann. Chem.463, 237 (1928).

    Google Scholar 

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  1. Lehrstuhl für organische Chemie, Chemischen Fakultät der Universität Sofia, Sofia, Bulgarien

    M. Kirilov & G. Petrov

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  1. M. Kirilov
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  2. G. Petrov
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Kirilov, M., Petrov, G. Darstellung, Struktur und Reaktionsfähigkeit einiger Metallderivate des Äthoxycarbonylmethan-phosphonsäurediäthylesters. Monatshefte für Chemie 103, 1651–1660 (1972). https://doi.org/10.1007/BF00904620

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  • DOI: https://doi.org/10.1007/BF00904620

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