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Phosphorylation ofN-trimethylsilyllactams

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Treatment ofN-trimethylsilyllactams with phosphoryl chlorides results in mixtures of products, whose formation can be explained by competition betweenN- andO-phosphorylation.

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References

  1. A. G. Shipov, E. A. Zheltonogova, V. P. Kobzareva, N. A. Orlova, and Yu. I. Baukov,Zh. Obshch. Khim., 1991,61, 2308 [J. Gen. Chem. USSR, 1991,61 (Engl. Transl.)].

    Google Scholar 

  2. H. Sasaki, Y. Mori, Y. Nakomura, and Y. Shibasaki,J. Med. Chem., 1991,34, 628.

    Google Scholar 

  3. W. J. Brouillette and G. L. Grunewald,J. Med. Chem., 1984,27, 202.

    Google Scholar 

  4. Jpn. Pat. 63215625;Chem. Abstrs., 1989,110, 75307.

  5. Jpn. Pat. 0222263;Chem. Abstrs., 1990,113, 40444.

  6. A. F. Grapov, L. V. Razvodovskaya, and N. N. Mel'nikov,Zh. Obshch. Khim., 1974,44, 281 [J. Gen. Chem. USSR, 1974,44 (Engl. Transl.)].

    Google Scholar 

  7. A. B. Uryupin, V. Yu. Komissarov, P. V. Petrovskii, Yu. A. Davidovich, T. A. Mastryukova, and M. I. Kabachnik,Izv. Akad. Nauk, Ser. Khim., 1992, 1694 [Bull. russ. Acad. Sci., Div. Chem. Sci., 1992,41, 1317 (Engl. Transl.)].

  8. M. M. Crutchfield, C. H. Dungan, J. H. Letcher, V. Mark, and G. R. Van Waser, inTopics in Phosphorus Chemistry, Eds. M. Grayson and E. J. Griffith, John Wiley & Sons, New York, 1967,5, 292, 316, 331.

    Google Scholar 

  9. A. D. F. Toy,J. Am. Chem. Soc., 1948,70, 3882.

    Google Scholar 

  10. A. S. Romakhin, I. M. Zaripov, Yu. G. Budnikova, Yu. A. Ignat'ev, E. V. Nikitin, A. P. Golikov, and Yu M. Kargin,Elektrokhimiya, 1989, 780 [Sov. Electrochem., 1989 (Engl. Transl.)].

  11. R. Mazurkiewicz,Acta Chim. Hung., 1989,116, 95.

    Google Scholar 

  12. A. I. Albanov, M. F. Larin, V. A. Pestunovich, M. G. Voronkov, E. P. Kramarova, and Yu. I. Baukov,Zh. Obshch. Khim., 1981,51, 488 [J. Gen. Chem. USSR, 1981,51 (Engl. Transl.)].

    Google Scholar 

  13. S. A. Matlin, P. G. Sommes, and R. M. Upton,J. Chem. Soc., Perkin Trans, 1, 1979, 2478.

    Google Scholar 

  14. P. R. Srinivasan, S. P. Gupta, and Shiang-Yuan Chen,J. Magn. Reson., 1983,46, 163.

    Google Scholar 

  15. A. N. Pudovik and M. G. Zimin,Usp. Khim., 1983,52, 1803 [Russ. Chem. Rev., 1982,52 (Engl. Transl.)].

    Google Scholar 

  16. A. J. Kirbi and S. G. Warren, inThe Organic Chemistry of Phosphorus, Elsevier, Amsterdam, 1967.

    Google Scholar 

  17. Comprehensive Organic Chemistry, Eds. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979,2, 1016.

    Google Scholar 

  18. R. Y. Ning, R. I. Fryer, P. B. Madan, and B. C. Sluboski,J. Org. Chem., 1976,41, 2720.

    Google Scholar 

  19. V. Misrahi and T. A. Modro,J. Org. Chem., 1982,47, 3533.

    Google Scholar 

  20. G. Etemad-Moghadam, A. Klaebe, and J. J. Perte,Phosp. and Sulf., 1981,12, 61.

    Google Scholar 

  21. W. C. Still, M. Kahn, and A. Mitra,J. Org. Chem., 1978,43, 2923.

    Google Scholar 

  22. B. P. Mundy, B. R. Larsen, L. F. McKenzie, and G. Braden,J. Org. Chem., 1972,37, 1635.

    Google Scholar 

  23. L. V. Razvodovskaya, A. F. Grapov, and N. N. Mel'nikov,Zh. Obshch. Khim., 1972,42, 1277 [J. Gen. Chem. USSR, 1972,42 (Engl. Transl.)].

    Google Scholar 

  24. M. Rothe and T. Toth,Chem. Ber., 1966,99, 3820.

    Google Scholar 

  25. F. Feher, G. Kuhlborsch, A. Blumcke, H. Keller, and K. Lippert,Chem. Ber., 1957,90, 134.

    Google Scholar 

  26. J. Michalski and T. Modro,Chem. Ber., 1962,95, 1629.

    Google Scholar 

  27. G. Sosnovsky and E. H. Zaret,Z. Naturforsch. B, 1976,316, 820.

    Google Scholar 

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1644–1648, September, 1994.

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Uryupin, A.B., Rakhov, I.A., Kolesova, V.A. et al. Phosphorylation ofN-trimethylsilyllactams. Russ Chem Bull 43, 1556–1560 (1994). https://doi.org/10.1007/BF00697149

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  • DOI: https://doi.org/10.1007/BF00697149

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