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Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives
Author(s) -
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
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100341
Subject(s) - chemistry , azide , reactivity (psychology) , double bond , nucleophilic substitution , organic chemistry , crystal structure , single crystal , nucleophile , medicinal chemistry , stereochemistry , catalysis , crystallography , medicine , alternative medicine , pathology
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.