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Organophosphorus chemistry, XII. Reaction of furil with alkyl phosphites and ylide-phosphoranes

Organophosphor-Chemie, 12. Mitt.: Reaktionen von Furil mit Alkylphosphiten und Ylid-Phosphoranen

  • Organische Chemie Und Biochemie
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Summary

The reaction of furil (1) with trialkyl phosphites2 yielded caged phosphorane derivatives of types3a-c. Dry hydrogen chloride gas converted3a-c into the respectivea-hydroxyvinyl-phosphates8a-c which are equally produced by reacting furil with the appropriate dialkyl phosphite7. The reaction of furil with ylide-phosphoranes10 proceeded according to the Wittig reaction mechanism to give the respective ethylenes11a-c. The new compounds have been characterized by their spectroscopic data (IR, PMR,31P-NMR, MS) and elementary analyses.

Zusammenfassung

Die Reaktion von Furil (1) mit Trialkylphosphiten2 ergab Phosphoranderivate des Typs3a-c. Trockenes Chlorwasserstoffgas setzte3a-c zu den entsprechendena-Hydroxyvinyl-phosphaten8a-c um, die auch bei der Reaktion von Furil mit dem entsprechenden Dialkylphosphit7 entstehen. Die Reaktion der Ylid-Phosphorane10 verlief nach dem Mechanismus der Wittig-Reaktion und ergab die entsprechenden Ethylene11a-c. Die neuen Verbindungen wurden mittels spektroskopischer Daten (IR, PMR,31P-NMR, MS) und der Elementaranalysen charakterisiert.

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References

  1. For part XI, cf.: Mahran M. R., Abdou W. M., Abd El-Rahman N. M., Sidky M. M. (in press) Phosphorus and Sulfur

  2. Kukhtin V. A. (1958) Dokl. Akad. Nauk SSSR121: 466; (1959) Chem. Abstr.53: 1105; Kukhtin V. A., Orekhova J. (1960) Zh. Obshch. Khim.30: 1208; (1960) Chem. Abstr.55: 358; Ramirez F., Desai N. B. (1963) J. Am. Chem. Soc.85: 3252

    Google Scholar 

  3. Kukhtin V. A., Kirillova K. M., Shagidullin R. R. (1962) Zh. Obshch. Khim.32: 649; (1963) Chem. Abstr.58: 546; Ogata Y., Yamashita M. (1970) J. Am. Chem. Soc.92: 4670

    Google Scholar 

  4. Ramirez F., Patwardhan A. V., Smith C. P. (1966) J. Org. Chem.31: 474; Ramirez F., Mitra R. B., Desai N. B. (1965) J. Am. Chem. Soc.82: 2651

    Google Scholar 

  5. Finar I. L. (1973) Organic Chemistry, Vol. 1: The Fundamental Principles, 6th edn. Longman, London, p. 850

    Google Scholar 

  6. Crutchfield M. M., Dungan O. H., Letcher J. H., Mark V., van Wazer I. R. (1967) Topics in Phosphorus Chemistry, Vol. 5:31P Nuclear Magnetic Resonance. Interscience, New York, chapt. 4

    Google Scholar 

  7. Ramirez F. (1968) Acc. Chem. Res.1: 168;

    Google Scholar 

  8. Abragan A. (1961) The Principle of Nuclear Magnetism. Clarendon Press, London

    Google Scholar 

  9. Williams D. H., Fleming I. (1966) Spectroscopic Methods in Organic Chemistry. McGraw-Hill, London, pp. 69, 126;

    Google Scholar 

  10. Silverstein R. M., Bassler G. C., Morrill T. C. (1981) Spectrometric Identification of Organic Compounds. Wiley, New York, chapt. 3, p. 229

    Google Scholar 

  11. Zbiral E. (1979) In: Cadogan J. I. G. (ed.) Organophosphorus Reagents in Organic Synthesis. Academic Press, London, chapt. 7, p. 304; Taylor R. J. K. (1977) Synthesis8: 564, 566; Cava M. P., Pohl R. J. (1960) J. Am. Chem. Soc.82: 5242

    Google Scholar 

  12. For reviews see (a) Emsley J., Hall D. (1976) The Chemistry of Phosphorus. Harper and Row, New York

    Google Scholar 

  13. Holmes R. R. (1980) Pentacoordinated Phosphorus, Vols. 1 and 2. American Chemical Society, Washington, DC

    Google Scholar 

  14. Chang L. L., Denney D. B., Denney D. Z., Kazior R. J. (1977) J. Am. Chem. Soc.99: 2293

    Google Scholar 

  15. Denney D. B., Denney D. Z., Hammond P. J., Huang C., Tseng K. S. (1980) J. Am. Chem. Soc.102: 5073

    Google Scholar 

  16. Denney D. B., Denney D. Z., Hammond P. J., Pin Wang Y. (1981) J. Am. Chem. Soc.103: 1785

    Google Scholar 

  17. Abdou W. M., Denney D. B., Denney D. Z., Pastor S. D. (1985) Phosphorus and Sulfur22: 99

    Google Scholar 

  18. Abdou W. M., Mahran M. R. (1986) Phosphorus and Sulfur26: 119

    Google Scholar 

  19. Abdou W. M., Mahran M. R., Hafez T. S., Sidky M. M. (1986) Phosphorus and Sulfur27: 345

    Google Scholar 

  20. Ramirez F., Desai N. B. (1960) J. Am. Chem. Soc.82: 2652; Sidky M. M., Abdou W. M. (1982) Egypt. J. Chem.25: 397

    Google Scholar 

  21. Hartman W. W., Dickey J. B. (1933) J. Am. Chem. Soc.55: 228

    Google Scholar 

  22. Kappe Th., Lender E., Ziegler E. (1968) Monatsh. Chem.99: 2157

    Google Scholar 

  23. Ramirez F., Dershowitz S. (1957) J. Org. Chem.22: 41

    Google Scholar 

  24. Michaelis A., Gleichmann L. (1882) Chem. Ber.15: 801

    Google Scholar 

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Authors and Affiliations

  1. Department of Pesticide Chemistry, National Research Centre, Cairo, Egypt

    Mohamed R. Mahran, Wafaa M. Abdou & Maha D. Khidre

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  1. Mohamed R. Mahran
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  2. Wafaa M. Abdou
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  3. Maha D. Khidre
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Dedicated to Prof. M. Sidky on the occasion of his 60th birthday

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Mahran, M.R., Abdou, W.M. & Khidre, M.D. Organophosphorus chemistry, XII. Reaction of furil with alkyl phosphites and ylide-phosphoranes. Monatsh Chem 121, 51–58 (1990). https://doi.org/10.1007/BF00810294

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  • DOI: https://doi.org/10.1007/BF00810294

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