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Stereospecific synthesis of bicyclic diaziridines: 4a-chloro-; 4e,6a- and 4a,6e-dichloro-5-methoxycarbonyl-1,6-diazabicyclo[3.1.0]hexanes

Sergei N Denisenko 1
Sergei N Denisenko
, 
Paul Rademacher 2
Paul Rademacher
, 
Remir Grigorevich Kostyanovsky 3
Remir Grigorevich Kostyanovsky
10.1070/MC1998v008n02ABEH000912
Published 1998-04-28
Communication , Volume 8, Issue 2, 54-56
8
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Denisenko S. N., Rademacher P., Kostyanovsky R. G. Stereospecific synthesis of bicyclic diaziridines: 4a-chloro-; 4e,6a- and 4a,6e-dichloro-5-methoxycarbonyl-1,6-diazabicyclo[3.1.0]hexanes // Mendeleev Communications. 1998. Vol. 8. No. 2. pp. 54-56.
GOST all authors (up to 50) Copy
Denisenko S. N., Rademacher P., Kostyanovsky R. G. Stereospecific synthesis of bicyclic diaziridines: 4a-chloro-; 4e,6a- and 4a,6e-dichloro-5-methoxycarbonyl-1,6-diazabicyclo[3.1.0]hexanes // Mendeleev Communications. 1998. Vol. 8. No. 2. pp. 54-56.
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TY - JOUR
DO - 10.1070/MC1998v008n02ABEH000912
UR - https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000912
TI - Stereospecific synthesis of bicyclic diaziridines: 4a-chloro-; 4e,6a- and 4a,6e-dichloro-5-methoxycarbonyl-1,6-diazabicyclo[3.1.0]hexanes
T2 - Mendeleev Communications
AU - Denisenko, Sergei N
AU - Rademacher, Paul
AU - Kostyanovsky, Remir Grigorevich
PY - 1998
DA - 1998/04/28
PB - Mendeleev Communications
SP - 54-56
IS - 2
VL - 8
ER -
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@article{1998_Denisenko,
author = {Sergei N Denisenko and Paul Rademacher and Remir Grigorevich Kostyanovsky},
title = {Stereospecific synthesis of bicyclic diaziridines: 4a-chloro-; 4e,6a- and 4a,6e-dichloro-5-methoxycarbonyl-1,6-diazabicyclo[3.1.0]hexanes},
journal = {Mendeleev Communications},
year = {1998},
volume = {8},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000912},
number = {2},
pages = {54--56},
doi = {10.1070/MC1998v008n02ABEH000912}
}
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Cite this
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Denisenko, Sergei N., et al. “Stereospecific synthesis of bicyclic diaziridines: 4a-chloro-; 4e,6a- and 4a,6e-dichloro-5-methoxycarbonyl-1,6-diazabicyclo[3.1.0]hexanes.” Mendeleev Communications, vol. 8, no. 2, Apr. 1998, pp. 54-56. https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000912.

Abstract

Amination of 2-methoxycarbonyl-3-chloro-1-pyrroline 1 with H2NOSO3H occurs predominantly from the anti side with respect to chlorine to afford the bicyclic diaziridine 2 with axial orientation of the 4-chloro substituent. Chlorination of 2 takes place exclusively in the 6-endo position to give 3a. 4,6-Dichlorodiaziridine is transformed from chair 3a into boat 3b as a result of endo–exo isomerization.

References

1.
10.1070/MC1998v008n02ABEH000912_bib1_1
Bespalov
Zh. Strukt. Khim., 1974
2.
10.1070/MC1998v008n02ABEH000912_bib1_2
Bespalov
Teor. Eksp. Khim., 1979
3.
10.1070/MC1998v008n02ABEH000912_bib2_1
Kuznetzov
Usp. Khim., 1979
4.
10.1070/MC1998v008n02ABEH000912_bib2_2
Kuznetzov
Zh. Org. Khim., 1979
5.
10.1070/MC1998v008n02ABEH000912_bib3
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1980
6.
10.1070/MC1998v008n02ABEH000912_bib4_1
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1981
7.
Asymmetrical nitrogen-40; Geminal systems-26 N-chlorohydrazines
Shustov G.V., Tavakalyan N.B., Kostyanovsky R.G.
Tetrahedron, 1985
8.
10.1070/MC1998v008n02ABEH000912_bib5
Shustov
Dokl. Akad. Nauk SSSR, 1986
9.
Barriers to inversion at nitrogen in bicyclic amines and hydrazines
Davies J.W., Malpass J.R., Moss R.E.
Tetrahedron Letters, 1985
10.
10.1070/MC1998v008n02ABEH000912_bib7
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1983
11.
Corrigenda
Denisenko S.N., Shustov G.V., Kostyananovsky R.G., Magnus P., Brown P.
Journal of the Chemical Society Chemical Communications, 1985
12.
10.1070/MC1998v008n02ABEH000912_bib9
Shustov
Khim. Geterotsikl. Soedin., 1986
13.
10.1070/MC1998v008n02ABEH000912_bib10
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1986
14.
10.1070/MC1998v008n02ABEH000912_bib11
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1988
15.
10.1070/MC1998v008n02ABEH000912_bib12
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1988
16.
10.1070/MC1998v008n02ABEH000912_bib13
Shustov
Izv. Akad. Nauk SSSR,Ser. Khim., 1988
18.
10.1070/MC1998v008n02ABEH000912_bib15
Shustov
Khim. Fiz., 1989
19.
Vicinal n,n interactions in N-chloro substituted diaziridines and oxaziridines: photoelectron spectra and electronic structures
Denisenko S.N., Rademacher P., Kowski K., Shustov G.V., Kostyanovsky R.G.
Journal of Molecular Structure, 1995
20.
Some novel reactions of N-chlorodifluoromethanimine
Zheng Y.Y., Bauknight C.W., DesMarteau D.D.
Journal of Organic Chemistry, 1984
21.
10.1070/MC1998v008n02ABEH000912_bib18
Khvostenko
Khim. Fiz., 1985
22.
Asymmetric nitrogen—41
Shustov G.V., Denisenko S.N., Chervin I.I., Asfandiarov N.L., Kostyanovsky R.G.
Tetrahedron, 1985
23.
10.1070/MC1998v008n02ABEH000912_bib20
Shustov
Izv. Akad. Nauk SSSR, Ser Khim., 1986
24.
10.1070/MC1998v008n02ABEH000912_bib21
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1986
25.
10.1070/MC1998v008n02ABEH000912_bib22
Shustov
Izv. Akad. Nauk SSSR, Ser. Khim., 1986
26.
10.1070/MC1998v008n02ABEH000912_bib23
Zolotoi
Izv. Akad. Nauk SSSR, Ser. Khim., 1986
27.
10.1070/MC1998v008n02ABEH000912_bib24
Kaupp
Izv. Akad. Nauk SSSR, Ser. Khim., 1991
28.
13C NMR spectra of tricyclic diaziridines and their data-base forecasts
Kaupp G., Denisenko S.N.
Magnetic Resonance in Chemistry, 1992
29.
The Reaction of Imines with Difluoramine. A Method of Preparation of Diazirines
Graham W.H.
Journal of the American Chemical Society, 1966
33.
10.1070/MC1998v008n02ABEH000912_bib30
Kostyanovsky
Khim.-Farm. Zh., 1986