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Mechanistic insight...
Mechanistic insight into self-propagation in organo-mediated Beckmann rearrangement: A combined experimental and computational study.
- Artikel/kapitelEngelska2013
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LIBRIS-ID:oai:gup.ub.gu.se/178364
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https://gup.ub.gu.se/publication/178364URI
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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.
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Tian, B.-X.
(författare)
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Pi, H.-J.
(författare)
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Eriksson, Leif A,1964Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology(Swepub:gu)xeleif
(författare)
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Deng, W.-P.
(författare)
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Göteborgs universitetInstitutionen för kemi och molekylärbiologi
(creator_code:org_t)
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Ingår i:Journal of Organic Chemistry78:9, s. 4297-43020022-32631520-6904
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