Wiley
Advanced Synthesis and Catalysis
,  volume 363 ,  issue 13 ,  pages 3365-3371

Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives

Akira YOSHIMURA 1, 2, 3
, 
Christopher D Huss 1
, 
Mackenzie Liebl 1
, 
Gregory Rohde 4
, 
Scott M Larson 1
, 
Gunnar B Frahm 1
, 
Mattew W Luedtke 5
, 
Tanner J Schumacher 1
, 
Zachary S Gardner 1
, 
Tsugio KITAMURA 6
, 
Akio Saito 7
, 
Viktor V Zhdankin 1
, 
Pavel S Postnikov 2, 8
, 
Mekhman S. Yusubov 2
1
 
2
 
3
 
Department of Chemistry and Biochemistry The College of St. Scholastica Duluth Minnesota 55811 USA | 
4
 
Marshall School Duluth Minnesota 55811 | 
5
 
6
 
7
 
8
 
Publication type: Journal Article
Publication date: 2021-05-28
Wiley
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
General Chemistry
Abstract

Pseudocyclic β‐trifluorosulfonyloxy vinylbenziodoxolones were prepared starting from hydroxybenziodoxolones and alkynes in the presence of trifluoromethanesulfonic acid. The reaction of these compounds with azide anion leads to β‐azido vinylbenziodoxolones as products of vinylic nucleophilic substitution in which addition‐elimination reactions occur and the double bond configuration is retained. The structures of β‐trifluorosulfonyloxy vinylbenziodoxolone and β‐azido vinylbenziodoxolone were established by single crystal X‐ray diffraction.

magnified image

Found 
Found 
1 citation
Beloglazkina Elena
DSc in Chemistry, professor
296 publications,  3 248 citations,  11 reviews
h-index: 29
Lomonosov Moscow State University
Lomonosov Moscow State University
1 citation
Luponosov Yuriy
🥼 🤝
DSc in Chemistry
113 publications,  2 526 citations,  13 reviews
h-index: 27
Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences
Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences
1 citation
Vil' Vera
PhD in Chemistry
86 publications,  1 967 citations,  3 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Organic Chemistry
1 citation
Yaremenko Ivan
PhD in Chemistry
60 publications,  1 567 citations,  5 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Organic Chemistry
1 citation
Gorbunova Yuliya
DSc in Chemistry, professor, full member of the Russian Academy of Sciences 
284 publications,  4 398 citations,  65 reviews
h-index: 34
Lomonosov Moscow State University
Lomonosov Moscow State University
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Lanthanides
Supramolecular chemistry
Tetrapyrrolic compounds
1 citation
Volcho Konstantin
DSc in Chemistry, professor of the Russian Academy of Sciences 
279 publications,  3 898 citations,  65 reviews
h-index: 31
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Danilkina Natalia
44 publications,  625 citations
h-index: 14
Saint Petersburg State University
Saint Petersburg State University
Research interests
Bioorganic chemistry
Click chemistry
Heterocyclic compounds
Medicinal Chemistry
Organic Chemistry
1 citation
Osipov Sergey
DSc in Chemistry
138 publications,  2 739 citations,  3 reviews
h-index: 29
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
1 citation
Gazizov Almir
🥼
DSc in Chemistry
157 publications,  889 citations,  23 reviews
h-index: 14
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Heterocyclic compounds
Organic Chemistry
Organophosphorus chemistry
1 citation
Karasik Andrey
DSc in Chemistry, professor, associate member of the Russian Academy of Sciences 
224 publications,  2 599 citations
h-index: 26
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Luminescence
Phosphorus ligands
1 citation
Dotsenko Viktor
DSc in Chemistry, professor
244 publications,  2 741 citations,  2 reviews
h-index: 22
North Caucasus Federal University
North Caucasus Federal University
Kuban State University
Kuban State University
Research interests
Active methylene compounds
Biological activity
Heterocyclic compounds
Malononitrile
Selenoamides
Thioamides
1 citation
Zagidullin Almaz
🥼 🤝
PhD in Chemistry
81 publications,  884 citations
h-index: 17
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Asymmetric metal complex catalysis
Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
Coordination chemistry of phosphorus
Organoelement chemistry
Organophosphorus chemistry
Synthesis of chiral phosphorus-containing ligands
1 citation
Aksenov Aleksandr
🥼 🤝
DSc in Chemistry, professor
243 publications,  2 187 citations,  15 reviews
h-index: 24
North Caucasus Federal University
North Caucasus Federal University
Research interests
Medicinal Chemistry
Organic Chemistry
1 citation
Sosnovskikh Vyacheslav
DSc in Chemistry, professor
355 publications,  4 721 citations
h-index: 30
Ural Federal University
Ural Federal University
1 citation
Ilkin Vladimir
PhD in Chemistry
16 publications,  187 citations
h-index: 7
Ural Federal University
Ural Federal University
Research interests
Catalysis
Heterocyclic compounds
Organic Chemistry
Synthetic Organic Chemistry
1 citation
Krylov Igor
PhD in Chemistry
78 publications,  1 885 citations,  18 reviews
h-index: 25
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Green chemistry
Organic Chemistry
Organic electrochemistry
Organic synthesis
Photochemistry
Plant protection
1 citation
Tikhomirov Alexander
🥼 🤝
DSc in Chemistry, associate professor
59 publications,  920 citations
h-index: 17
Mendeleev University of Chemical Technology of Russia
Mendeleev University of Chemical Technology of Russia
Gause Institute of New Antibiotics
Gause Institute of New Antibiotics
Research interests
Medicinal Chemistry
1 citation
Ivanov Andrey
54 publications,  534 citations
h-index: 12
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Buev Evgeny
PhD in Chemistry
31 publications,  346 citations,  2 reviews
h-index: 9
Ural Federal University
Ural Federal University
Research interests
Chemistry of nitrogen-containing heterocycles
Organic Chemistry
Organic synthesis

Top-30

Journals

1
Molecules
Molecules, 1, 7.14%
Molecules
1 publication, 7.14%
European Journal of Organic Chemistry
European Journal of Organic Chemistry, 1, 7.14%
European Journal of Organic Chemistry
1 publication, 7.14%
Angewandte Chemie
Angewandte Chemie, 1, 7.14%
Angewandte Chemie
1 publication, 7.14%
Angewandte Chemie - International Edition
Angewandte Chemie - International Edition, 1, 7.14%
Angewandte Chemie - International Edition
1 publication, 7.14%
New Journal of Chemistry
New Journal of Chemistry, 1, 7.14%
New Journal of Chemistry
1 publication, 7.14%
Organic and Biomolecular Chemistry
Organic and Biomolecular Chemistry, 1, 7.14%
Organic and Biomolecular Chemistry
1 publication, 7.14%
Chemical Science
Chemical Science, 1, 7.14%
Chemical Science
1 publication, 7.14%
Journal of Organic Chemistry
Journal of Organic Chemistry, 1, 7.14%
Journal of Organic Chemistry
1 publication, 7.14%
Frontiers in Chemistry
Frontiers in Chemistry, 1, 7.14%
Frontiers in Chemistry
1 publication, 7.14%
Organic Letters
Organic Letters, 1, 7.14%
Organic Letters
1 publication, 7.14%
Russian Chemical Reviews
Russian Chemical Reviews, 1, 7.14%
Russian Chemical Reviews
1 publication, 7.14%
Chemical Reviews
Chemical Reviews, 1, 7.14%
Chemical Reviews
1 publication, 7.14%
Yakugaku Zasshi
Yakugaku Zasshi, 1, 7.14%
Yakugaku Zasshi
1 publication, 7.14%
Synthesis
Synthesis, 1, 7.14%
Synthesis
1 publication, 7.14%
1

Publishers

1
2
3
Wiley
Wiley, 3, 21.43%
Wiley
3 publications, 21.43%
Royal Society of Chemistry (RSC)
Royal Society of Chemistry (RSC), 3, 21.43%
Royal Society of Chemistry (RSC)
3 publications, 21.43%
American Chemical Society (ACS)
American Chemical Society (ACS), 3, 21.43%
American Chemical Society (ACS)
3 publications, 21.43%
MDPI
MDPI, 1, 7.14%
MDPI
1 publication, 7.14%
Frontiers Media S.A.
Frontiers Media S.A., 1, 7.14%
Frontiers Media S.A.
1 publication, 7.14%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 7.14%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 7.14%
Pharmaceutical Society of Japan
Pharmaceutical Society of Japan, 1, 7.14%
Pharmaceutical Society of Japan
1 publication, 7.14%
Georg Thieme Verlag KG
Georg Thieme Verlag KG, 1, 7.14%
Georg Thieme Verlag KG
1 publication, 7.14%
1
2
3
  • We do not take into account publications without a DOI.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
14
Share
Cite this
GOST |
Cite this
GOST Copy
YOSHIMURA A. et al. Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives // Advanced Synthesis and Catalysis. 2021. Vol. 363. No. 13. pp. 3365-3371.
GOST all authors (up to 50) Copy
YOSHIMURA A., Huss C. D., Liebl M., Rohde G., Larson S. M., Frahm G. B., Luedtke M. W., Schumacher T. J., Gardner Z. S., KITAMURA T., Saito A., Zhdankin V. V., Postnikov P. S., Yusubov M. S. Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives // Advanced Synthesis and Catalysis. 2021. Vol. 363. No. 13. pp. 3365-3371.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/adsc.202100341
UR - https://doi.org/10.1002/adsc.202100341
TI - Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives
T2 - Advanced Synthesis and Catalysis
AU - YOSHIMURA, Akira
AU - Huss, Christopher D
AU - Liebl, Mackenzie
AU - Rohde, Gregory
AU - Larson, Scott M
AU - Frahm, Gunnar B
AU - Luedtke, Mattew W
AU - Schumacher, Tanner J
AU - Gardner, Zachary S
AU - KITAMURA, Tsugio
AU - Saito, Akio
AU - Zhdankin, Viktor V
AU - Postnikov, Pavel S
AU - Yusubov, Mekhman S.
PY - 2021
DA - 2021/05/28
PB - Wiley
SP - 3365-3371
IS - 13
VL - 363
SN - 1615-4150
SN - 1615-4169
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2021_YOSHIMURA,
author = {Akira YOSHIMURA and Christopher D Huss and Mackenzie Liebl and Gregory Rohde and Scott M Larson and Gunnar B Frahm and Mattew W Luedtke and Tanner J Schumacher and Zachary S Gardner and Tsugio KITAMURA and Akio Saito and Viktor V Zhdankin and Pavel S Postnikov and Mekhman S. Yusubov},
title = {Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives},
journal = {Advanced Synthesis and Catalysis},
year = {2021},
volume = {363},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/adsc.202100341},
number = {13},
pages = {3365--3371},
doi = {10.1002/adsc.202100341}
}
MLA
Cite this
MLA Copy
YOSHIMURA, Akira, et al. “Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives.” Advanced Synthesis and Catalysis, vol. 363, no. 13, May. 2021, pp. 3365-3371. https://doi.org/10.1002/adsc.202100341.