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

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

YOSHIMURA Akira 1, 2, 3
Saito Akio 6
Yusubov Mekhman S. 1
Huss Christopher D 3
Liebl Mackenzie 3
Larson Scott M 3
Frahm Gunnar B 3
Luedtke Mattew W 7
Schumacher Tanner J 3
Gardner Zachary S 3
KITAMURA Tsugio 8
Zhdankin Viktor V 3
2
 
Department of Chemistry and Biochemistry The College of St. Scholastica Duluth Minnesota 55811 USA
3
 
Department of Chemistry and Biochemistry University of Minnesota Duluth Minnesota 55812 USA
5
 
Marshall School Duluth Minnesota 55811
6
 
Division of Applied Chemistry Institute of Engineering Tokyo University of Agriculture and Technology 2-23-16 Naka-cho Koganei Tokyo 184-8588
7
 
Masonic Cancer Center University of Minnesota Minnesota 55455 USA
8
 
Department of Chemistry and Applied Chemistry Saga University, Honjo-machi Saga 840-8502 Japan
Publication typeJournal Article
Publication date2021-05-28
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.4
ISSN16154150, 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

Citations by journals

1
Molecules
Molecules, 1, 11.11%
Molecules
1 publication, 11.11%
European Journal of Organic Chemistry
European Journal of Organic Chemistry, 1, 11.11%
European Journal of Organic Chemistry
1 publication, 11.11%
Angewandte Chemie
Angewandte Chemie, 1, 11.11%
Angewandte Chemie
1 publication, 11.11%
Angewandte Chemie - International Edition
Angewandte Chemie - International Edition, 1, 11.11%
Angewandte Chemie - International Edition
1 publication, 11.11%
New Journal of Chemistry
New Journal of Chemistry, 1, 11.11%
New Journal of Chemistry
1 publication, 11.11%
Organic and Biomolecular Chemistry
Organic and Biomolecular Chemistry, 1, 11.11%
Organic and Biomolecular Chemistry
1 publication, 11.11%
Chemical Science
Chemical Science, 1, 11.11%
Chemical Science
1 publication, 11.11%
Journal of Organic Chemistry
Journal of Organic Chemistry, 1, 11.11%
Journal of Organic Chemistry
1 publication, 11.11%
Frontiers in Chemistry
Frontiers in Chemistry, 1, 11.11%
Frontiers in Chemistry
1 publication, 11.11%
1

Citations by publishers

1
2
3
Wiley
Wiley, 3, 33.33%
Wiley
3 publications, 33.33%
Royal Society of Chemistry (RSC)
Royal Society of Chemistry (RSC), 3, 33.33%
Royal Society of Chemistry (RSC)
3 publications, 33.33%
Multidisciplinary Digital Publishing Institute (MDPI)
Multidisciplinary Digital Publishing Institute (MDPI), 1, 11.11%
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 11.11%
American Chemical Society (ACS)
American Chemical Society (ACS), 1, 11.11%
American Chemical Society (ACS)
1 publication, 11.11%
Frontiers Media S.A.
Frontiers Media S.A., 1, 11.11%
Frontiers Media S.A.
1 publication, 11.11%
1
2
3
  • We do not take into account publications that without a DOI.
  • Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
  • Statistics recalculated weekly.
Metrics
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%2Fadsc.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 00:00:00
PB - Wiley
SP - 3365-3371
IS - 13
VL - 363
SN - 1615-4150
SN - 1615-4169
ER -
BibTex |
Cite this
BibTex 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%2Fadsc.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%2Fadsc.202100341.
Found error?