Mechanistic Insights into the Palladium-Induced Domino Reaction Leading to Ketones from Benzyl β-Ketoesters:  First Characterization of the Enol as an Intermediate

The monitoring by UV spectroscopy of the Pd-catalyzed hydrogenolysis in acetonitrile of 2-methyl-2-benzyloxycarbonyl-1-indanone and 2-methyl-2-benzyloxycarbonyl-1-tetralone showed the successive formation of corresponding β-ketoacids and enols to deliver finally the ketones. Some factors which influ...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-10, Vol.69 (20), p.6528-6532
Main Authors: Detalle, Jean-François, Riahi, Abdelkhalek, Steinmetz, Vincent, Hénin, Françoise, Muzart, Jacques
Format: Article
Language:English
Subjects:
Chemical Sciences
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:The monitoring by UV spectroscopy of the Pd-catalyzed hydrogenolysis in acetonitrile of 2-methyl-2-benzyloxycarbonyl-1-indanone and 2-methyl-2-benzyloxycarbonyl-1-tetralone showed the successive formation of corresponding β-ketoacids and enols to deliver finally the ketones. Some factors which influence the stability of the intermediates are determined. In contrast to the above benzyl β-ketoesters, the enol was not detected from benzyl (2-methylinden-3-yl) carbonate.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049464w