Article (Scientific journals)
Transition-Metal-Catalyzed Reactions of Diazo Compounds. 2.1 Addition to Aromatic Molecules: Catalysis of Buchner's Synthesis of Cycloheptatrienes
Anciaux, A. J.; Demonceau, Albert; Noels, Alfred et al.
1981In Journal of Organic Chemistry, 46 (5), p. 873-876
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Abstract :
[en] The addition of carbenes (generated from diazo esters) to aromatic molecules is efficiently catalyzed at room temperature by electron-poor Rh(II) carboxylates [tetrakis(perfluorocarboxylato)dirhodium(II)]. The reaction gives ready access to 1-carbalkoxycyclohepta-2,4,6-trienes (the kinetic nonconjugated isomer) in very good yield. The observed regioselectivities are rationalized in terms of an attack of a highly electrophilic carbenoid species on the aromatic molecule. A competitive reduction of the catalyst simultaneously occurs and is responsible for a slow deactivation of the system. © 1981, American Chemical Society. All rights reserved.
Disciplines :
Chemistry
Author, co-author :
Anciaux, A. J.;  Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liége, Sart Tilman, 4000 Liége, Belgium, United States
Demonceau, Albert ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Noels, Alfred ;  Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Hubert, André J.
Warin, Roger ;  Université de Liège - ULiège > Département de géologie > Minéralogie et cristallochimie
Teyssié, Philippe ;  Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Language :
English
Title :
Transition-Metal-Catalyzed Reactions of Diazo Compounds. 2.1 Addition to Aromatic Molecules: Catalysis of Buchner's Synthesis of Cycloheptatrienes
Publication date :
1981
Journal title :
Journal of Organic Chemistry
ISSN :
0022-3263
eISSN :
1520-6904
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Volume :
46
Issue :
5
Pages :
873-876
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 29 June 2019

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