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- Bielawski, Christopher W.
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Alkyne and Reversible Nitrile Activation: N,N '-Diamidocarbene-Facilitated Synthesis of Cyclopropenes, Cyclopropenones, and Azirines
- Author(s)
- Moerdyk, Jonathan P., Bielawski, Christopher W.
- Issued Date
- 2012-04
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.134, no.14, pp.6116 - 6119
- Abstract
- We report the synthesis of a variety of diamidocyclopropenes by combining an isolable and readily accessible N,N'-diamidocarbene (DAC) with a range of alkynes (nine examples, 68-97% yield). Subsequent hydrolysis of selected cyclopropenes afforded the corresponding cyclopropenones or alpha,beta-unsaturated acids, depending on the reaction conditions. In addition, the combination of a DAC with alkyl or aryl nitriles was found to form 2H-azirines in a reversible manner (four examples, K-eq = 4-72 M-1 at 30 degrees C in toluene).
- Publisher
- AMER CHEMICAL SOC
- ISSN
- 0002-7863
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