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Formation of 1,2,4-oxadiazoles in the course of photooxidation of aromatic azides in acetonitrile

Ekaterina Mikhailovna Chainikova 1
Ekaterina Mikhailovna Chainikova
, 
Marat F Abdullin 1
Marat F Abdullin
, 
Alexander Nikolaevich Lobov 1
Alexander Nikolaevich Lobov
, 
Aigul Nakipovna Teregulova 1
Aigul Nakipovna Teregulova
, 
Rustam Lutfullovich Safiullin 1
Rustam Lutfullovich Safiullin
10.1016/j.mencom.2021.03.029
Published 2021-03-03
Communication , Volume 31, Issue 2, 233-235
5
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Chainikova E. M. et al. Formation of 1,2,4-oxadiazoles in the course of photooxidation of aromatic azides in acetonitrile // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 233-235.
GOST all authors (up to 50) Copy
Chainikova E. M., Abdullin M. F., Lobov A. N., Teregulova A. N., Safiullin R. L. Formation of 1,2,4-oxadiazoles in the course of photooxidation of aromatic azides in acetonitrile // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 233-235.
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TY - JOUR
DO - 10.1016/j.mencom.2021.03.029
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.029
TI - Formation of 1,2,4-oxadiazoles in the course of photooxidation of aromatic azides in acetonitrile
T2 - Mendeleev Communications
AU - Chainikova, Ekaterina Mikhailovna
AU - Abdullin, Marat F
AU - Lobov, Alexander Nikolaevich
AU - Teregulova, Aigul Nakipovna
AU - Safiullin, Rustam Lutfullovich
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 233-235
IS - 2
VL - 31
ER -
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@article{2021_Chainikova,
author = {Ekaterina Mikhailovna Chainikova and Marat F Abdullin and Alexander Nikolaevich Lobov and Aigul Nakipovna Teregulova and Rustam Lutfullovich Safiullin},
title = {Formation of 1,2,4-oxadiazoles in the course of photooxidation of aromatic azides in acetonitrile},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.029},
number = {2},
pages = {233--235},
doi = {10.1016/j.mencom.2021.03.029}
}
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Chainikova, Ekaterina Mikhailovna, et al. “Formation of 1,2,4-oxadiazoles in the course of photooxidation of aromatic azides in acetonitrile.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 233-235. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.029.

Keywords

1,2,4-oxadiazoles
aryl azides
aryl nitroso oxides
nitrile oxides
photooxidation

Abstract

Photolysis of aryl azides at room temperature in acetonitrile in the presence of oxygen proceeds as arene ring opening and acetonitrile trapping to afford 5-methyl-3-(5-oxopenta-1,3-dien-1-yl)-1,2,4-oxadiazoles. In the case of 4-methoxyphenyl azide, a product depriving of acetonitrile reactant, 1-hydroxyimino-3-methylcyclopentadiene-2-carbaldehyde, is also formed.

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