Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 43, Pages 11575-11578Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406505
Keywords
carbanions; fluorine; NMR spectroscopy; reaction mechanisms; reactive intermediates
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Funding
- Loker Hydrocarbon Research Institute
- Office of Naval Research
- Defense Threat Reduction Agency
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The trifluoromethanide anion is the postulated key intermediate in nucleophilic trifluoromethylation reactions. However, for more than six decades, the trifluoromethanide anion was widely believed to exist only as a short-lived transient species in the condensed phase. It has now been prepared in bulk for the first time in THF solution. The trifluoromethanide anion with the [K(18-crown-6)](+) cation was unequivocally characterized by low-temperature F-19 and (CNMR)-C-13 spectroscopy. Its intermediacy in nucleophilic trifluoromethylation reactions was directly evident by its reaction chemistry with various electrophilic substrates. Variable-temperature NMR spectroscopy, along with quantum mechanical calculations, support the persistence of the trifluoromethanide anion.
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