Conclusions
-
1.
We have synthesized 1-alkoxyaziridine-2,2-dicarboxylic esters by reaction of alkoxyamines with diethyl α,β-dibromomethylmalonate and studied their PMR and mass spectra.
-
2.
We have established the trans-stereospecificity of the amination and saponification of l-alkoxyaziridine-2,2-dicarboxylic esters.
-
3.
We have studied the kinetics of the equilibrium cis-trans isomerization of unsymmetrically substituted derivatives of 1-alkoxyaziridine-2,2-dicarboxylic acids.
Similar content being viewed by others
Literature cited
R. G. Kostyanovskii, G. V. Shustov, A. I. Mishchenko, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., 2026 (1976).
R. G. Kostyanovskii, A. V. Prosyanik, V. I. Markov, A. I. Zon, and A. E. Polyakov, Izv. Akad. Nauk SSSR, Ser. Khim., 418 (1974); 1559 (1976); Fifth International Congress of Heterocyclic Chemistry, Abstracts of Papers, University of Ljubljana, Yugoslavia, July 13–18, 1975, p. 267.
R. G. Kostyanovskii, V. F. Rudchenko, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., 1685 (1975); 2621 (1975).
A. N. Zaidel', Elementary Estimation of Experimental Errors [in Russian], Nauka, Leningrad (1968), p. 64.
J. M. Lehn, Topics in Current Chemistry,15, 311 (1970).
G. Hirsch, in: Collected Problems in Stereochemistry [Russian translation], Mir (1970), p. 199; F. R. Jensen and C. H. Bushweller, Advances in Alicyclic Chemistry,3, 139 (1971).
D. Crepaux and J. M. Lehn, Mol. Phys.,14, 547 (1968);16, 225 (1969).
H. Paulsen and W. Grewe, Chem. Ber.,103, 486 (1970); A. A. Fomichev and R. G. Kostyanovskii, Dokl. Akad. Nauk SSSR,199, 1110 (1971); M. Ueyama and K. Tori, J. Chem. Soc. Jpn., Pure Chem. Sec.,92, 741 (1971): W. B. Jennings, D. R. Boyd, C. G. Watson, E. D. Becker, R. B. Bradley, and D. M. Jerina, J. Am. Chem. Soc.,94, 8501 (1972).
G. Karabatsos, R. A. Taller, and F. M. Vane, J. Am. Chem. Soc.,85, 2326 (1963).
T. Yonezawa, I. Morishima, and K. Fukuta, Bull. Chem. Soc. Jpn.,40, 1807 (1967);41, 2297 (1968); J. L. Pierre, P. Barret, and P. Arnaud, Bull. Soc. Chim. France, 3619 (1971).
H. Booth, Progr. NMR Spectroscopy,5, 149 (1969); V. F. Bystrov, Usp. Khim.,41, 512 (1972).
R. G. Kostyanovskii, A. I. Ermakov, Kh. Khafizov, and G. K. Kadorkina, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 2646.
R. Ya. Levina and N. N. Gorovikov, Zh. Obshch. Khim.,25, 986 (1955).
Beilsteins Handbuch der organischen Chemie, vierte Auflage, Vol. II, 631 (1920).
G. R. Clemo and K. N. Welch, J. Chem. Soc., 2621 (1928).
Author information
Authors and Affiliations
Additional information
For Part 10, see [1].
Translated from Izvestiya Akademiya Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 628–638., March, 1977.
Rights and permissions
About this article
Cite this article
Kostyanovskii, R.G., Rudchenko, V.F. & Prosyanik, A.V. Asymmetric nonbridgehead nitrogen. Russ Chem Bull 26, 565–574 (1977). https://doi.org/10.1007/BF01179468
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01179468