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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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.)].
H. Sasaki, Y. Mori, Y. Nakomura, and Y. Shibasaki,J. Med. Chem., 1991,34, 628.
W. J. Brouillette and G. L. Grunewald,J. Med. Chem., 1984,27, 202.
Jpn. Pat. 63215625;Chem. Abstrs., 1989,110, 75307.
Jpn. Pat. 0222263;Chem. Abstrs., 1990,113, 40444.
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.)].
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.)].
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.
A. D. F. Toy,J. Am. Chem. Soc., 1948,70, 3882.
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.)].
R. Mazurkiewicz,Acta Chim. Hung., 1989,116, 95.
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.)].
S. A. Matlin, P. G. Sommes, and R. M. Upton,J. Chem. Soc., Perkin Trans, 1, 1979, 2478.
P. R. Srinivasan, S. P. Gupta, and Shiang-Yuan Chen,J. Magn. Reson., 1983,46, 163.
A. N. Pudovik and M. G. Zimin,Usp. Khim., 1983,52, 1803 [Russ. Chem. Rev., 1982,52 (Engl. Transl.)].
A. J. Kirbi and S. G. Warren, inThe Organic Chemistry of Phosphorus, Elsevier, Amsterdam, 1967.
Comprehensive Organic Chemistry, Eds. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979,2, 1016.
R. Y. Ning, R. I. Fryer, P. B. Madan, and B. C. Sluboski,J. Org. Chem., 1976,41, 2720.
V. Misrahi and T. A. Modro,J. Org. Chem., 1982,47, 3533.
G. Etemad-Moghadam, A. Klaebe, and J. J. Perte,Phosp. and Sulf., 1981,12, 61.
W. C. Still, M. Kahn, and A. Mitra,J. Org. Chem., 1978,43, 2923.
B. P. Mundy, B. R. Larsen, L. F. McKenzie, and G. Braden,J. Org. Chem., 1972,37, 1635.
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.)].
M. Rothe and T. Toth,Chem. Ber., 1966,99, 3820.
F. Feher, G. Kuhlborsch, A. Blumcke, H. Keller, and K. Lippert,Chem. Ber., 1957,90, 134.
J. Michalski and T. Modro,Chem. Ber., 1962,95, 1629.
G. Sosnovsky and E. H. Zaret,Z. Naturforsch. B, 1976,316, 820.
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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