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N-Chloro-N-alkoxyureas: synthesis, structure and properties

Vasiliy Georgievich Shtamburg 1
Vasiliy Georgievich Shtamburg
, 
Oleg Valer'ievich Shishkin 2
Oleg Valer'ievich Shishkin
, 
Roman Igorevich Zubatyuk 2
Roman Igorevich Zubatyuk
, 
Svetlana V Kravchenko 1
Svetlana V Kravchenko
, 
Alexander Valerievich Tsygankov 1
Alexander Valerievich Tsygankov
, 
Alexander Vladimirovich Mazepa 3
Alexander Vladimirovich Mazepa
, 
Evgeny A Klots 4
Evgeny A Klots
, 
Remir Grigorevich Kostyanovsky 5
Remir Grigorevich Kostyanovsky
1 Department of Chemistry, Dnepropetrovsk National University, Dnepropetrovsk, Ukraine
2 STC 'Institute for Single Crystals', National Academy of Sciences of Ukraine, Kharkov, Ukraine
3 A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, Ukraine
4 Kirovograd State Pedagogical University, Kirovograd, Ukraine
10.1070/MC2006v016n06ABEH002382
Published 2006-12-06
Communication , Volume 16, Issue 6, 323-325
23
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Shtamburg V. G. et al. N-Chloro-N-alkoxyureas: synthesis, structure and properties // Mendeleev Communications. 2006. Vol. 16. No. 6. pp. 323-325.
GOST all authors (up to 50) Copy
Shtamburg V. G., Shishkin O. V., Zubatyuk R. I., Kravchenko S. V., Tsygankov A. V., Mazepa A. V., Klots E. A., Kostyanovsky R. G. N-Chloro-N-alkoxyureas: synthesis, structure and properties // Mendeleev Communications. 2006. Vol. 16. No. 6. pp. 323-325.
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TY - JOUR
DO - 10.1070/MC2006v016n06ABEH002382
UR - https://mendcomm.colab.ws/publications/10.1070/MC2006v016n06ABEH002382
TI - N-Chloro-N-alkoxyureas: synthesis, structure and properties
T2 - Mendeleev Communications
AU - Shtamburg, Vasiliy Georgievich
AU - Shishkin, Oleg Valer'ievich
AU - Zubatyuk, Roman Igorevich
AU - Kravchenko, Svetlana V
AU - Tsygankov, Alexander Valerievich
AU - Mazepa, Alexander Vladimirovich
AU - Klots, Evgeny A
AU - Kostyanovsky, Remir Grigorevich
PY - 2006
DA - 2006/12/06
PB - Mendeleev Communications
SP - 323-325
IS - 6
VL - 16
ER -
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@article{2006_Shtamburg,
author = {Vasiliy Georgievich Shtamburg and Oleg Valer'ievich Shishkin and Roman Igorevich Zubatyuk and Svetlana V Kravchenko and Alexander Valerievich Tsygankov and Alexander Vladimirovich Mazepa and Evgeny A Klots and Remir Grigorevich Kostyanovsky},
title = {N-Chloro-N-alkoxyureas: synthesis, structure and properties},
journal = {Mendeleev Communications},
year = {2006},
volume = {16},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2006v016n06ABEH002382},
number = {6},
pages = {323--325},
doi = {10.1070/MC2006v016n06ABEH002382}
}
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Shtamburg, Vasiliy Georgievich, et al. “N-Chloro-N-alkoxyureas: synthesis, structure and properties.” Mendeleev Communications, vol. 16, no. 6, Dec. 2006, pp. 323-325. https://mendcomm.colab.ws/publications/10.1070/MC2006v016n06ABEH002382.

Abstract

The XRD studies of N-chloro-N-alkoxyureas 1, 2 have revealed the high pyramidality of the amide nitrogen in the O–N–Cl group caused by nO–O*N–Cl anomeric effect, the other sequence of this effect is anionic lability of the chlorine atom; nucleophilic substitution at the nitrogen depends on the N′-substitutent nature: chlorine atoms in ureas 1 and 5 are replaced by outer nucleophile whereas, under the same conditions, ureas 2–4 undergo cyclization into 1-alkoxybenzimidazolin-2-ones 10–12.

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