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Long-Lived Trifluor...
Long-Lived Trifluoromethanide Anion: A Key Intermediate in Nucleophilic Trifluoromethylations.
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Prakash, G. K. Surya (author)
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Wang, F. (author)
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Zhang, Zhe (author)
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Haiges, Ralf (author)
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Rahm, Martin, 1982 (author)
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Christe, Karl O. (author)
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Mathew, Thomas (author)
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Olah, George A. (author)
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- 2014-08-21
- 2014
- English.
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In: Angewandte Chemie - International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 53:43, s. 11575-11578
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https://doi.org/10.1...
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Abstract
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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 prepd. in bulk for the first time in THF soln. The trifluoromethanide anion with the [K(18-crown-6)]+ cation was unequivocally characterized by low-temp. 19F and 13C NMR spectroscopy. Its intermediacy in nucleophilic trifluoromethylation reactions was directly evident by its reaction chem. with various electrophilic substrates. Variable-temp. NMR spectroscopy, along with quantum mech. calcns., support the persistence of the trifluoromethanide anion. [on SciFinder(R)]
Subject headings
- NATURVETENSKAP -- Kemi -- Oorganisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Inorganic Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- fluorine
- reaction mechanisms
- reactive intermediates
- NMR spectroscopy
- carbanions
Publication and Content Type
- art (subject category)
- ref (subject category)
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