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Palladium(0)-Catalyzed Cycloisomerization of Enallenes.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Manuskript (Annet vitenskapelig)
Identifikatorer
URN: urn:nbn:se:su:diva-22606OAI: oai:DiVA.org:su-22606DiVA, id: diva2:189149
Merknad
Part of urn:nbn:se:su:diva-100Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07 Sist oppdatert: 2010-01-13bibliografisk kontrollert
Inngår i avhandling
1. Palladium-Catalyzed Carbocyclizations of Allenes with Unsaturated Hydrocarbons
Åpne denne publikasjonen i ny fane eller vindu >>Palladium-Catalyzed Carbocyclizations of Allenes with Unsaturated Hydrocarbons
2004 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi, 2004. s. 53
Emneord
Palladium-catalysis, Allenes
HSV kategori
Identifikatorer
urn:nbn:se:su:diva-100 (URN)91-7265-863-0 (ISBN)
Disputas
2004-04-29, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Veileder
Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07bibliografisk kontrollert

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