Conclusions
-
1.
Alkaline hydrolysis of N,N-dialkoxy-N′,N′-dimethylureas gives NH-dialkoxyamines.
-
2.
N-Hydroxymethyl- and N-aminomethyl-N,N,-dialkoxyamines have been synthesized and their reactions with nucleophiles and electrophiles have been studied.
-
3.
The configurational stability of the N atom in NH-dialkoxyamines and their derivatives has been determined by NMR.
Similar content being viewed by others
Literature cited
I. I. Chervin, V. S. Nosova, V. F. Rudchenko, V. I. Shevchenko, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1148 (1986).
G. N. Sausen, US Patent 3214465 (1965); Chem. Abstr.,64, 3350e (1966).
R. G. Kostyanovsky (Kostyanovskii), V. F. Rudchenko, V. G. Shtamburg, I. I. Chervin, and Sh. S. Nasibov, Tetrahedron,34, 4245 (1981).
V. F. Rudchenko, V. I. Shevchenko, S. M. Ignatov, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2411 (1983).
V. F. Rudchenko, V. I. Shevchenko, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 598 (1986).
V. F. Rudchenko, V. G. Shtamburg, A. P. Pleshkova, Sh. S. Nasibov, I. I. Chervin, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2539 (1981).
D. I. Mendeleev, Foundations of Chemistry [in Russian], 6th edn. (1895), p. 210; J. E. T. Corrie, G. W. Kirby, A. E. Laird, L. W. Machinnon, and J. K. Tyler, J. Chem. Soc. Chem. Commun., 275 (1978); F. W. Dalby, Can. J. Phys.,36, 1336 (1958); M. E. Jacox and F. L. Rook, J. Phys. Chem.,86, 2899 (1982).
F. Raschig, Sulfur and Nitrogen Studies [in German], Verlag Chemie. Leipzig, Berlin (1924), p. 83.
L. Radom, W. J. Hehre, and J. A. Pople, J. Am. Chem. Soc.,93, 289 (1971).
M. A. Shokhen, A. V. Eremeev, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 347 (1985).
N. B. Karlstédt, M. V. Proskurina, and I. F. Lutsenko, Zh. Obshch. Khim.,42, 2418 (1972).
A. V. Fokin, Yu. M. Kosyrev, and V. I. Shevchenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1831 (1982).
G. Zinner, W. Kliegel, and W. Ritter, Angew Chem.,75, 640 (1963).
H. Böhme and M. Haake, in: Advances in Organic Chemistry. Methods and Results, E. C. Taylor (ed.), Interscience (1976), p. 107.
R. G. Kostyanovskii and O. A. Pan'shin, Izv. Akad. Nauk SSSR, Ser. Khim., 740 (1965).
R. G. Kostyanovskii, O. A. Pan'shin, and T. Z. Papoyan, Dokl. Akad. Nauk SSSR,177, 1099 (1967).
R. G. Kostyanovskii and O. A. Pan'shin, Izv. Akad. Nauk SSSR, Ser. Khim., 564 (1965).
R. G. Kostyanovskii, O. A. Yuzhakova, and V. F. Bystrov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1666 (1962).
V. F. Bystrov, R. G. Kostyanovskii, O. A. Pan'shin, A. U. Stepanyants, and O. A. Yuzhakova, Opt. Spektrosk.,19, 217 (1965).
J. M. Lehn, Topics Current Chem.,15, 311 (1970).
G. Binsch, J. B. Lambert, B. W. Roberts, and J. D. Roberts, J. Am. Chem. Soc.,86, 5564 (1964).
A. V. Bogatskii, N. G. Luk'yanenko, V. N. Pastushok, and R. G. Kostyanovskii, Dokl. Akad. Nauk SSSR,265, 619 (1982); Synthesis, 992 (1983).
Author information
Authors and Affiliations
Additional information
For preceding communications, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1153–1160, May, 1986.
Rights and permissions
About this article
Cite this article
Rudchenko, V.F., Ignatov, S.M., Chervin, I.I. et al. Asymmetric nitrogen Communication 48. Geminal systems. communication 32 NH-dialkoxyamines: synthesis, mydroxy-and aminomethylation, nmr spectra, and configurational stability. Russ Chem Bull 35, 1045–1052 (1986). https://doi.org/10.1007/BF00955378
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00955378