RESEARCH HIGHLIGHT

Metal-Catalyzed Cyclization Reactions of Carbonyl Ylides:  Synthesis and DFT Study of Mechanisms

Organometallics

2007

Mehmet A. Celik, Mine Yurtsever, Nurcan Ş. Tüzün, Füsun Ş. Güngör, Özkan Sezer, Olcay Anaç

TOC

1,3-Dioxole derivatives were synthesized by the reaction of 3-methylenebicyclo[2.2.1]heptan-2-one and dimethyl diazomalonate with Cu(acac)2 as catalyst. All of the possible mechanisms of copper-catalyzed cycloaddition reactions leading to dioxole and dihydrofuran derivatives have been investigated extensively at B3LYP/6-31G(d) level. It has been concluded that the nature of the substrate and the stability of the carbonyl ylide are the dominant factors in determining the product distribution.

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