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

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 substit...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-07, Vol.363 (13), p.3365-3371
Main Authors: Yoshimura, Akira, Huss, Christopher D., Liebl, Mackenzie, Rohde, Gregory T., Larson, Scott M., Frahm, Gunnar B., Luedtke, Mattew W., Schumacher, Tanner J., Gardner, Zachary S., Zhdankin, Viktor V., Postnikov, Pavel S., Yusubov, Mekhman S., Kitamura, Tsugio, Saito, Akio
Format: Article
Language:English
Subjects:
alkenyliodonium
Alkynes
Crystals
hypervalent iodine
Micheal acceptor
pseudocyclic
Single crystals
Substitution reactions
Triflic acid
vinylbenziodoxolones
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100341