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Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene

Stanislav Alekseevich Paveliev 1
Stanislav Alekseevich Paveliev
, 
Oleg Olegovich Segida 1
Oleg Olegovich Segida
, 
Uliana Vladimirovna Fedorova 2
Uliana Vladimirovna Fedorova
,  , 
10.1016/j.mencom.2022.03.004
Published 2022-03-06
Communication , Volume 32, Issue 2, 167-169
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Paveliev S. A. et al. Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 167-169.
GOST all authors (up to 50) Copy
Paveliev S. A., Segida O. O., Fedorova U. V., Mulina O. M., Terent'ev A. O. Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 167-169.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.004
TI - Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene
T2 - Mendeleev Communications
AU - Paveliev, Stanislav Alekseevich
AU - Segida, Oleg Olegovich
AU - Fedorova, Uliana Vladimirovna
AU - Mulina, Olga Mikhailovna
AU - Terent'ev, Alexander Olegovich
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 167-169
IS - 2
VL - 32
ER -
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@article{2022_Paveliev,
author = {Stanislav Alekseevich Paveliev and Oleg Olegovich Segida and Uliana Vladimirovna Fedorova and Olga Mikhailovna Mulina and Alexander Olegovich Terent'ev},
title = {Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.004},
number = {2},
pages = {167--169},
doi = {10.1016/j.mencom.2022.03.004}
}
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Paveliev, Stanislav Alekseevich, et al. “Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 167-169. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.004.

Keywords

N-hydroxyphthalimide
N-oxyl radicals
free radicals
hypervalent iodine
imides
vinyl azides

Abstract

O,O′-Bis(phthalimido)-modified 2-(hydroxyimino)ethanols containing N–O–N fragment were synthesized in high yields via the reaction of vinyl azides with N-hydroxyphthalimide under the action of hypervalent iodine-based oxidant. The reaction proceeds under mild conditions and is compatible with a wide range of vinyl azides. Presumably, the process starts with the oxidative formation of phthalimide-N-oxyl radical, followed by its addition to vinyl azide with the subsequent trapping of the generated iminyl radical with the second phthalimide-N-oxyl radical.

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