Elucidation of Carbene Ambiphilicity Leading to the Discovery of Reversible Ammonia Activation
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- Elucidation of Carbene Ambiphilicity Leading to the Discovery of Reversible Ammonia Activation
- Moerdyk, Jonathan P.; Blake, Garrett A.; Chase, Daniel T.; Bielawski, Christopher W.
- Aromatic amines; Aryl amines; Carbenes; Electrophilic activation; Organic reagents; Primary amines; Relative rates
- Issue Date
- AMER CHEMICAL SOC
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.135, no.50, pp.18798 - 18801
- An N,N′-diamidocarbene (DAC) was found to activate a broad range of primary as well as secondary aliphatic and aromatic amines. The relative rates measured for the insertion of the DAC into the primary amines were consistent with an electrophilic activation mechanism; in contrast, the DAC functioned as a nucleophile upon treatment with secondary aryl amines. Collectively, these results constituted the first ambiphilic process for an isolable carbene. By comparison, an analogous diaminocarbene was found to serve exclusively as a nucleophile under similar conditions and led to the discovery of the first organic reagent to reversibly activate ammonia.
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