Synthesis 2006(16): 2697-2706  
DOI: 10.1055/s-2006-942507
PAPER
© Georg Thieme Verlag Stuttgart · New York

Five- and Six-Membered Nickelacyclic Carboxylates as Reagents for the Facile Synthesis of δ-Ketocarboxylic Acids, Isocoumarins, and 1,3-Dicarbonyl Derivatives­ of Benzoic Acid

Jens Langer, Martin Gärtner, Helmar Görls, Dirk Walther*
Department of Inorganic and Analytical Chemistry, University of Jena, 07743 Jena, Germany
e-Mail: Dirk.Walther@uni-jena.de;
Weitere Informationen

Publikationsverlauf

Received 6 April 2006
Publikationsdatum:
19. Juli 2006 (eFirst)

Abstract

The nickelacyclic carboxylates A and B reacted with α-halo ketones to form α,β-unsaturated δ-ketocarboxylic acids which were easily converted into pyranones or isocoumarins. In addition, reaction of the nickelacyclic acyl derivative C with α-halo ketones resulted in the formation of substituted 1,3-dicarbonyl compounds with a benzoic acid substituent in the 1-position. In these reactions, many functional groups were tolerated.

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CCDC-602921 (A), CCDC-602922 (B), CCDC-602923 (D), CCDC-602924 (2a), CCDC-602925 (2b′), CCDC-602926 (2c′), CCDC-602927 (2f′), CCDC-602928 (2g), CCDC-602929 (2h′), CCDC-602930 (3a), CCDC-602931 (3b), CCDC-602932 (3d), CCDC-602933 (3f), CCDC-602934 (3g), CCDC-602935 (3h′), CCDC-602936 (4f), CCDC-602937 (4i), CCDC-602938 (5a), CCDC-602939 (5c), CCDC-602940 (5g′) and CCDC-602941 (6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK, fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk].