Reactions of 1‐Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects
Publication type: Journal Article
Publication date: 2018-02-02
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
New substituted 1-arylbenziodoxolones were prepared and their reactivity with azide anion nucleophile was investigated. It was found that independent on the presence of substituents, all reactions of 1-arylbenziodoxolones proceed as nucleophilic substitution of the iodonium leaving group in the electron-deficient benziodoxolone benzene ring. The presence of bulky substituents in the ortho-position of the aryl ring slowers the reaction, while the presence of a moderately electron-withdrawing bromine substituent in the para-position to iodine in the benziodoxolone ring moderately increases the rate of substitution. The presence of a strongly electron-withdrawing nitro group in the para-position to iodine in the benziodoxolone ring dramatically increases the rate of substitution. These observations are in agreement with the electronic requirements for internal nucleophilic substitution in the benziodoxole ring. A quantum-chemical computational study of the possible reaction paths is in agreement with the observed effects of substituents on the reactivity of arylbenziodoxolones in this reaction.
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Citations from 2024:
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GOST
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Yusubov M. S. et al. Reactions of 1‐Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects // European Journal of Organic Chemistry. 2018. Vol. 2018. No. 5. pp. 640-647.
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Yusubov M. S., Soldatova N., Postnikov P. S., Valiev R. R., Svitich D. Y., Yusubova R. Y., YOSHIMURA A., Wirth T., Zhdankin V. V. Reactions of 1‐Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects // European Journal of Organic Chemistry. 2018. Vol. 2018. No. 5. pp. 640-647.
Cite this
RIS
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TY - JOUR
DO - 10.1002/ejoc.201701595
UR - https://doi.org/10.1002/ejoc.201701595
TI - Reactions of 1‐Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects
T2 - European Journal of Organic Chemistry
AU - Yusubov, Mekhman S
AU - Soldatova, Natalia
AU - Postnikov, Pavel S.
AU - Valiev, R. R.
AU - Svitich, Dmitry Y
AU - Yusubova, Roza Y
AU - YOSHIMURA, Akira
AU - Wirth, Thomas
AU - Zhdankin, Viktor V.
PY - 2018
DA - 2018/02/02
PB - Wiley
SP - 640-647
IS - 5
VL - 2018
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2018_Yusubov,
author = {Mekhman S Yusubov and Natalia Soldatova and Pavel S. Postnikov and R. R. Valiev and Dmitry Y Svitich and Roza Y Yusubova and Akira YOSHIMURA and Thomas Wirth and Viktor V. Zhdankin},
title = {Reactions of 1‐Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects},
journal = {European Journal of Organic Chemistry},
year = {2018},
volume = {2018},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/ejoc.201701595},
number = {5},
pages = {640--647},
doi = {10.1002/ejoc.201701595}
}
Cite this
MLA
Copy
Yusubov, Mekhman S., et al. “Reactions of 1‐Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects.” European Journal of Organic Chemistry, vol. 2018, no. 5, Feb. 2018, pp. 640-647. https://doi.org/10.1002/ejoc.201701595.