Article (Scientific journals)
Transition-Metal-Catalyzed Reactions of Diazo Compounds. 1. Cyclopropanation of Double Bonds
Anciaux, A. J.; Hubert, André J.; Noels, Alfred et al.
1980In Journal of Organic Chemistry, 45 (4), p. 695-702
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Abstract :
[en] Rhodium(II) and palladium(II) carboxylates are efficient catalysts for the cyclopropanation of olefins by diazo esters. Intramolecular competitions within diolefins and intermolecular competitions between pairs of monoolefins showed quite different cyclopropanation selectivities with the above-mentioned metal derivatives. Rhodium essentially promotes a carbenoid mechanism involving an electrophilic attack of uncomplexed olefins, while a determinant olefin coordination is observed with palladium. By comparison, the classical copper derivatives are essentially borderline cases: most often they behave as carbenoid catalysts, except when associated with very weak ligands such as in copper triflate. The synthetic usefulness of these reactions is emphasized in terms of their high efficiency and regioselectivity. © 1980, American Chemical Society. All rights reserved.
Disciplines :
Chemistry
Author, co-author :
Anciaux, A. J.;  Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liége, Tilman, 4000 Liege, United States
Hubert, André J.
Noels, Alfred ;  Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Petiniot, N.;  Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liége, Tilman, 4000 Liege, United States
Teyssié, Philippe ;  Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Language :
English
Title :
Transition-Metal-Catalyzed Reactions of Diazo Compounds. 1. Cyclopropanation of Double Bonds
Publication date :
1980
Journal title :
Journal of Organic Chemistry
ISSN :
0022-3263
eISSN :
1520-6904
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Volume :
45
Issue :
4
Pages :
695-702
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 29 June 2019

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