Abstract
The phosphorylation ofN-trimethylsilyllactams by phosphorus(III) acid chlorides results in correspondingN-phosphinolactams in high yields. The derivatives thus obtained have been used in the synthesis ofN-phosphoryl- andN-thiophosphoryllactams. The reversibility of the reaction of phosphinolactams has been established.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. B. Ouryupin, I. A. Rakhov, V. A. Kolesova, P. V. Petrovskii, T. A. Mastryukova, and M. I. Kabachnik,Izv. Akad. Nauk, Ser. Khim., 1994, 1644 [Russ. Chem. Bull., 1994,43, 1556 (Engl. Transl.)]
G. Just, D. Dugat, and W.-Y. Liu,Can. J. Chem., 1983,61, 1730.
W. H. Koster, R. Zahler, H. W. Chang, C. M. Cimarusti, G. A. Jacobs, and M. Perri,J. Am. Chem. Soc., 1983,105, 3743.
D. J. Hart, K.-l. Kanai, D. G. Thomas, and T.-K. Yang,J. Org. Chem., 1983,48, 289.
D. M. Malenko, L. I. Nesterova, S. N. Luk'yanenko, L. V. Randina, and A. D. Sinitsa,Zh. Obshch. Khim., 1993,63, 1675 [J. Gen. Chem., 1993,63 (Engl. Transl.)].
M. Cypryk, J. Chojnowski, and J. Michalski,Tetrahedron, 1985,41, 2471.
M. K. Grachev, V. Yu. Mishina, and E. E. Nifant'ev,Zh. Obshch. Khim., 1993,63, 1671 [J. Gen. Chem., 1993,63 (Engl. Transl.)].
M. A. Pudovik. L. K. Kibardina, M. D. Medvedeva. N. P. Anoshina, T. A. Pestova. and A. N. Pudovik,Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 672 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1977,26 (Engl. Transl.)].
M. A. Pudovik, L. K. Kibardina, and A. N. Pudovik,Zh. Obshch. Khim., 1991,61, 1058 [J. Gen. Chem. USSR, 1991,61 (Engl. Transl.)].
M. Rothe and T. Toth,Chem. Bsr., 1966,99, 3820.
G. M. Kosolapoff and R. M. Watson,J. Am. Chem. Soc., 1951,73, 4101.
H. McCombie, B. C. Saunders. and G. J. Stacey,J. Chem. Soc., 1945, 380.
H. J. Lucas, F. W. Mitchell, Jr., and C. N. Scully,J. Am. Chem. Soc., 1950,72, 5491.
H. G. Cook, J. D. Ilett, B. C. Saunders, G. J. Stacey, H. G. Watson, I. G. E. Wilding, and S. G. Woodcock,J. Chem. Soc., 1949, 2921.
Author information
Authors and Affiliations
Additional information
For communication 1 see Ref. 1.
Translated fromIzyestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2250–2255, November, 1995.
Rights and permissions
About this article
Cite this article
Ouryupin, A.B., Rakhov, I.A., Kolesova, V.A. et al. N-Phosphorylated lactams. Russ Chem Bull 44, 2157–2162 (1995). https://doi.org/10.1007/BF00696723
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00696723