Abstract
The reaction of N-trimethylsilyl derivatives of amides and imides with alkyl sulfonates on heating affords the corresponding N-alkyl derivatives and trimethylsilyl sulfonates.
References
R. E. Benson, Th. L. Cairns, J. Am. Chem. Soc., 1948, 70, 2115.
H. Bredereck, F. Effenberger, G. Simehen, Ber., 1963, 96, 1350.
H. Bredereck, R. Gompper, H. Rempfer, K. Klem, H. Kuk, Ber., 1959, 92, 329.
M. Matsui, Mem. Coll. Sci. Eng. Kyoto, 1909, 2, 37.
A. Buhner. Ann. Chem., 1904, 333, 289.
R. Gommper, Chem. Ber., 1960, 93, 187.
J. W. Ralls, J. Org. Chem., 1961, 21, 66.
H. Bohme, G. Berg, Chem. Ber., 1966, 99, 2127.
R. Roger, D. G. Neilson, Chem. Rev., 1961, 61, 179.
E. P. Kramarova, A. G. Shipov, N. A. Anisimova, N. A. Orlova, O. B. Artamkina, I. Yu. Belavin, Yu. I. Baukov, J. Gen. Chem. USSR (Engl. Transl.), 1988, 58, 970.
A. G. Shipov, E. P. Kramarova, N. A. Kalashnikova, E. A. Besova, Yu. I. Baukov, Russ. J. Gen. Chem. (Engl. Transl.), 1997, 67, 1736.
E. A. Zheltonogova, N. A. Orlova, V. P. Kobzareva, A. G. Shipov, Yu. I. Baukov, J. Gen. Chem. USSR (Engl. Transl.), 1991, 61, 2092.
N. A. Anisimova, E. P. Kramarova, I. Yu. Belavin, Yu. I. Baukov, J. Gen. Chem. USSR (Engl. Transl.), 1986, 56, 1631.
N. A. Anisimova, Abstract of Ph. D. Theses, MGPI, Moscow, 1983, 16 p. (in Russian).
N. A. Orlova, I. Yu. Belavin, V. N. Sergeev, A. G. Shipov, Yu. I. Baukov, J. Gen. Chem. USSR (Engl. Transl.), 1984, 54, 635.
A. G. Shipov, N. A. Orlova, I. A. Savot’yanov, O. B. Artamkina, Yu. I. Baukov, J. Gen. Chem. USSR (Engl. Transl.), 1989, 59, 959.
A. G. Shipov, E. P. Kramarova, V. V. Negrebetsky, V. I. Akhapkina, S. A. Pogozhykh, Ui. I. Baukov, Vestnik RGMU, 2006, No 1, 56.
A. I. Albanov, M. F. Larin, V. A. Pestunovich, M. G. Voronkov, E. P. Kramarova, Yu. I. Baukov, Zh. Obshch. Khim., 1981, 51, 488.(in Russian).
K. A. Andrianov, A. I. Nogaydeli, D. Sh. Akhobadze, L. M. Khananashvili, L. Sh. Tkeshelashvili, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1972, 41, 1100.
K. Ruhlman, B. Ruppert, Lieb. Ann., 1965, 686, 226.
S. A. Pogozhykh, Yu. E. Ovchinnikov, E. P. Kramarova, Vad. V. Negrebetsky, A. G. Shipov, A. I. Albanov, M. G. Voronkov, V. A. Pestunovich, I. Yu. Baukov, Russ. J. Gen. Chem., 2004, 74, 1501.
F. Lutsenko, Yu. I. Baukov, A. S. Kostyuk, N. I. Savelyeva, V. K. Krysina, J. Organomet. Chem., 1969, 17, 241.
V. Bazant, V. Chvalovsky, J. Rathousky, Organosilicon Compounds, Czechoslovakia, Prague, 1973, 4, 31.
L. Craig, J. Am. Chem. Soc., 1933, 55, 295.
A. G. Shipov, Yu. I. Baukov, J. Gen. Chem. USSR (Engl. Transl.), 1984, 54, 1642.
E. P. Kramarova, N. A. Anisimova, Yu. I. Baukov, J. Gen. Chem. USSR (Engl. Transl.), 1991, 61, 1284.
N. J. Leonard, A. B. Simon, J. Org. Chem., 1952, 17, 1262.
J. H. Padon, H. Adkins, J. Am. Chem. Soc., 1936, 58, 2487.
C. S. Marvel, W. W. Moyer, J. Org. Chem., 1957, 22, 1065.
G. Tsolomiti, K. Tsolomiti, A. Tsolomitis, Heterocycl. Commun., 2006, 12, 179.
W. Titherley, J. Chem. Soc., Trans., 1901, 79, 391.
J. Barluenga, F. Arnar, R. Lis, R. Rodes, Chem. Soc., Perkin Trans.1, 1980, 2732.
Author information
Authors and Affiliations
Corresponding author
Additional information
Based on the materials of the 5th EuChemS Inorganic Chemistry Conference (EICC-5) (June 24—28, 2019, Moscow, Russa).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0398—0400, February, 2020.
Rights and permissions
About this article
Cite this article
Shagina, A.D., Kramarova, E.P., Shipov, A.G. et al. N-Alkylation of N-trimethylsilyl derivatives of lactams, amides, and imides with alkyl sulfonates. Russ Chem Bull 69, 398–400 (2020). https://doi.org/10.1007/s11172-020-2775-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-020-2775-x