Chemistry - A European Journal, volume 23, issue 67, pages 17037-17047
Fused 1,2,3-Thiaselenazoles Synthesized from 1,2,3-Dithiazoles through Selective Chalcogen Exchange
Konstantinova Lidia S.
1, 2
,
Baranovsky Ilia V
2
,
Pritchina Elena A.
3, 4
,
Mikhailov Maksim S
1
,
Bagryanskaya Irina Yu.
3, 5
,
Semenov Nikolay
5
,
Irtegova Irina G
5
,
Salnikov Georgi E
3, 5
,
Gritsan N.P
4, 7
,
Zibarev Andrey V.
5, 7, 8
,
Rakitin Oleg A.
1, 2
1
Publication type: Journal Article
Publication date: 2017-11-08
Journal:
Chemistry - A European Journal
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 4.3
ISSN: 09476539, 15213765
General Chemistry
Catalysis
Organic Chemistry
Abstract
A new approach to the synthesis of fused 1,2,3-thiaselenazoles-rare five-membered heterocycles that contain two different chalcogens-from the corresponding 1,2,3-dithiazoles and SeO2 was accomplished by selective exchange of S and Se atoms. The fused carbo- and heterocyclic units were indene, naphthalenone, cyclohexadienone, cyclopentadiene, benzoannulene, and benzoxazine. The molecular structures of two of the thiaselenadiazole products and one of the dithiazole precursors were confirmed by single-crystal X-ray diffraction. The reaction is highly solvent selective; it only takes place in solvents that contain a C=O group (e.g., DMF or tetramethylurea). According to DFT calculations, the reaction is thermodynamically favorable. Based on the DFT calculations and 77 Se NMR spectroscopy, two tentative mechanisms that feature isomeric transition states and intermediates are suggested for the reaction via ring-opening addition of SeO2 to the S-X dithiazole bond (X=N or S). The DFT-calculated first adiabatic electron affinities of the compounds were chalcogen independent and positive in all cases, which assumes formation of thermodynamically stable radical anions (RAs). These calculated RAs featured either normal or abnormal elongation of the S1-X2 (X=S or Se) bond relative to their neutral precursors and possessed π* or σ* SOMOs, respectively.
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Konstantinova L. S. et al. Fused 1,2,3-Thiaselenazoles Synthesized from 1,2,3-Dithiazoles through Selective Chalcogen Exchange // Chemistry - A European Journal. 2017. Vol. 23. No. 67. pp. 17037-17047.
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Konstantinova L. S., Baranovsky I. V., Pritchina E. A., Mikhailov M. S., Bagryanskaya I. Y., Semenov N., Irtegova I. G., Salnikov G. E., Lyssenko K. A., Gritsan N., Zibarev A. V., Rakitin O. A. Fused 1,2,3-Thiaselenazoles Synthesized from 1,2,3-Dithiazoles through Selective Chalcogen Exchange // Chemistry - A European Journal. 2017. Vol. 23. No. 67. pp. 17037-17047.
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TY - JOUR
DO - 10.1002/chem.201703182
UR - https://doi.org/10.1002%2Fchem.201703182
TI - Fused 1,2,3-Thiaselenazoles Synthesized from 1,2,3-Dithiazoles through Selective Chalcogen Exchange
T2 - Chemistry - A European Journal
AU - Konstantinova, Lidia S.
AU - Baranovsky, Ilia V
AU - Pritchina, Elena A.
AU - Mikhailov, Maksim S
AU - Rakitin, Oleg A.
AU - Bagryanskaya, Irina Yu.
AU - Semenov, Nikolay
AU - Irtegova, Irina G
AU - Salnikov, Georgi E
AU - Lyssenko, Konstantin A.
AU - Gritsan, N.P
AU - Zibarev, Andrey V.
PY - 2017
DA - 2017/11/08 00:00:00
PB - Wiley
SP - 17037-17047
IS - 67
VL - 23
SN - 0947-6539
SN - 1521-3765
ER -
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@article{2017_Konstantinova,
author = {Lidia S. Konstantinova and Ilia V Baranovsky and Elena A. Pritchina and Maksim S Mikhailov and Oleg A. Rakitin and Irina Yu. Bagryanskaya and Nikolay Semenov and Irina G Irtegova and Georgi E Salnikov and Konstantin A. Lyssenko and N.P Gritsan and Andrey V. Zibarev},
title = {Fused 1,2,3-Thiaselenazoles Synthesized from 1,2,3-Dithiazoles through Selective Chalcogen Exchange},
journal = {Chemistry - A European Journal},
year = {2017},
volume = {23},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002%2Fchem.201703182},
number = {67},
pages = {17037--17047},
doi = {10.1002/chem.201703182}
}
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Konstantinova, Lidia S., et al. “Fused 1,2,3-Thiaselenazoles Synthesized from 1,2,3-Dithiazoles through Selective Chalcogen Exchange.” Chemistry - A European Journal, vol. 23, no. 67, Nov. 2017, pp. 17037-17047. https://doi.org/10.1002%2Fchem.201703182.