期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 50, 页码 18798-18801出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja411467p
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资金
- National Science Foundation [CHE-0645563]
- University of Texas at Austin
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1266323] Funding Source: National Science Foundation
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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