Nucleophilic trifluoromethylthiolation of organoselenocyanates with trifluoromethanesulfenamide reagent: Access to CF3SSe-containing compounds

[Display omitted] •New fluorinated groups bring innovative properties.•Association of trifluoromethyl group with heteroatoms is of great interest.•Trifluoromethylthio group possesses specific properties.•Combination of CF3S group with chalcogens modulate properties. Trifluoromethanesulfenamide reage...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2018-06, Vol.210, p.112-116
Main Authors: Glenadel, Quentin, Ayad, Camille, D’Elia, Marc-Alexandre, Billard, Thierry, Toulgoat, Fabien
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
Organoselenocyanate
Trifluoromethanesufenamide
Trifluoromethylthiolation
Trifluoromethylthioselenide
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Summary:[Display omitted] •New fluorinated groups bring innovative properties.•Association of trifluoromethyl group with heteroatoms is of great interest.•Trifluoromethylthio group possesses specific properties.•Combination of CF3S group with chalcogens modulate properties. Trifluoromethanesulfenamide reagent, initially designed as electrophilic reagent, can be considered as a trifluoromethylthio anion source in presence of tetrabutylammonium iodide. Herein, we report the reaction of trifluoromethanesulfenamide with organoselenocyanates to prepare under mild conditions compounds bearing a new fluorinated group, namely SeSCF3.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2018.03.009