期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 43, 页码 11575-11578出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406505
关键词
carbanions; fluorine; NMR spectroscopy; reaction mechanisms; reactive intermediates
资金
- Loker Hydrocarbon Research Institute
- Office of Naval Research
- Defense Threat Reduction Agency
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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