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Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2003 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, Vol. 125, no 46, 14140-14148 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2003. Vol. 125, no 46, 14140-14148 p.
URN: urn:nbn:se:su:diva-22601OAI: diva2:189144
Part of urn:nbn:se:su:diva-100Available from: 2004-04-07 Created: 2004-04-07 Last updated: 2009-10-07Bibliographically approved
In thesis
1. Palladium-Catalyzed Carbocyclizations of Allenes with Unsaturated Hydrocarbons
Open this publication in new window or tab >>Palladium-Catalyzed Carbocyclizations of Allenes with Unsaturated Hydrocarbons
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Palladium-catalyzed reactions of unsaturated hydrocarbons are important processes in organic chemistry especially for the generation of ring systems. This thesis describes the development and mechanistic studies of carbocyclization reactions of allenes with olefins, allyls or 1,3-dienes catalyzed by palladium(0)- and palladium(II)-complexes. These reactions generally exhibit high stereo- and regioselectivity and give rise to stereodefined [n,3,0] bicyclic systems (n=3,4,5,6) in good to excellent yields. The mechanisms for these reactions were investigated with special attention directed to the intramolecular reaction of (π-allyl)palladium(II)-complexes and (π-1,3-diene)palladium(II)-complexes with allenes. It was demonstrated that the carbon-carbon bond formation occurred by nucleophilic attack of the middle carbon atom of the allene on the face of the allyl or 1,3-diene opposite to that of the palladium atom. Further, two new types of oxidative palladium(II)-catalyzed reactions between allenes and olefins or 1,3-dienes have been developed. These cyclizations constitute a new type of carbon-carbon bond forming reaction and there are support for a palladium(II)-catalyzed C-H activation at the allenic moiety rendering a vinylidienepalladium-intermediate followed by carbon-carbon bond formation via insertion of the olefin or 1,3-diene.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2004. 53 p.
Palladium-catalysis, Allenes
National Category
Organic Chemistry
urn:nbn:se:su:diva-100 (URN)91-7265-863-0 (ISBN)
Public defence
2004-04-29, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Available from: 2004-04-07 Created: 2004-04-07Bibliographically approved

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Bäckvall, Jan-E
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