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Mechanistic insight into self-propagation in organo-mediated Beckmann rearrangement: A combined experimental and computational study.
- An, N. (author)
- Tian, B.-X. (author)
- Pi, H.-J. (author)
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- Deng, W.-P. (author)
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- (creator_code:org_t)
- 2013
- 2013
- English.
- In: Journal of Organic Chemistry. - 0022-3263 .- 1520-6904. ; 78:9, s. 4297-4302
- Journal article (peer-reviewed)
Abstract
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- Organo-mediated Beckmann rearrangement in the liquid phase, which has the advantage of high efficiency and straightforward experimental procedures, plays an important role in the synthesis of amides from oximes. However, the catalytic mechanisms of these organic-based promoters are still not well understood. In this work, we report a combined experimental and computational study on the mechanism of Beckmann rearrangement mediated by organic-based promoters, using TsCl as an example. A novel self-propagating cycle is proposed, and key intermediates of this self-propagating cycle are confirmed by both experiments and DFT calculations. In addition, the reason why cyclohexanone oxime is not a good substrate of the organo-mediated Beckmann rearrangement is discussed, and a strategy for improving the yield is proposed.
Subject headings
- NATURVETENSKAP -- Kemi -- Polymerkemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Polymer Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Fysikalisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Physical Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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- art (subject category)
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- An, N.
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- and Chemical Science ...
- and Theoretical Chem ...
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- University of Gothenburg
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