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A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate

Remir Grigorevich Kostyanovsky 1
Remir Grigorevich Kostyanovsky
, 
Anatoly Georgievich Korepin 2
Anatoly Georgievich Korepin
, 
Pavel Vasil'evich Galkin 2
Pavel Vasil'evich Galkin
, 
Yuri Il'ich Èl'natanov 1
Yuri Il'ich Èl'natanov
, 
Gulnara Konstantinovna Kadorkina 1
Gulnara Konstantinovna Kadorkina
, 
Ivan Ivanovich Chervin 1
Ivan Ivanovich Chervin
, 
Vasily Remirovich Kostyanovsky 1
Vasily Remirovich Kostyanovsky
10.1070/MC1995v005n06ABEH000532
Published 1995-12-31
Communication , Volume 5, Issue 6, 216-217
7
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Kostyanovsky R. G. et al. A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate // Mendeleev Communications. 1995. Vol. 5. No. 6. pp. 216-217.
GOST all authors (up to 50) Copy
Kostyanovsky R. G., Korepin A. G., Galkin P. V., Èl'natanov Y. I., Kadorkina G. K., Chervin I. I., Kostyanovsky V. R. A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate // Mendeleev Communications. 1995. Vol. 5. No. 6. pp. 216-217.
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TY - JOUR
DO - 10.1070/MC1995v005n06ABEH000532
UR - https://mendcomm.colab.ws/publications/10.1070/MC1995v005n06ABEH000532
TI - A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate
T2 - Mendeleev Communications
AU - Kostyanovsky, Remir Grigorevich
AU - Korepin, Anatoly Georgievich
AU - Galkin, Pavel Vasil'evich
AU - Èl'natanov, Yuri Il'ich
AU - Kadorkina, Gulnara Konstantinovna
AU - Chervin, Ivan Ivanovich
AU - Kostyanovsky, Vasily Remirovich
PY - 1995
DA - 1995/12/31
PB - Mendeleev Communications
SP - 216-217
IS - 6
VL - 5
ER -
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@article{1995_Kostyanovsky,
author = {Remir Grigorevich Kostyanovsky and Anatoly Georgievich Korepin and Pavel Vasil'evich Galkin and Yuri Il'ich Èl'natanov and Gulnara Konstantinovna Kadorkina and Ivan Ivanovich Chervin and Vasily Remirovich Kostyanovsky},
title = {A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate},
journal = {Mendeleev Communications},
year = {1995},
volume = {5},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1995v005n06ABEH000532},
number = {6},
pages = {216--217},
doi = {10.1070/MC1995v005n06ABEH000532}
}
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Kostyanovsky, Remir Grigorevich, et al. “A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate.” Mendeleev Communications, vol. 5, no. 6, Dec. 1995, pp. 216-217. https://mendcomm.colab.ws/publications/10.1070/MC1995v005n06ABEH000532.

Abstract

Partial cis-N-halogenation of methyl 2-aziridinecarboxylate (Azy–OMe) takes place only under conditions of intramolecular hydrogen bond breaking under the action of F2 in the presence of Et3N, and also under the action of KOCI in the presence of H2O; for the N-fluoro derivative, a record high nitrogen inversion barrier was found (ΔG#35 kcal mol–1).

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