Metal Ion Catalyzed Reactions of Acrylonitrile, Acrylamide, and Ethyl Acrylate by way of Their Diels-Alder Cycloadducts

Article abstract of DOI:10.1021/ja00240a037

In this paper, we report our successful efforts in coupling a cycloaddition/cycloreversion sequence to the well-documented metal ion promotion of functional group conversion in the cases of acrylonitrile to acrylamide, acrylamide to ethyl acrylate, and ethyl acrylate to acrylic acid.With 9-(2-pyridyl)anthracene as the diene, cycloadducts were prepared that underwent metal-promoted nitrile hydration, ethyl ester hydrolysis, and amide alcoholysis reactions.In addition, we report the synthesis of 9,10-bis(((2-(dimethylamino)ethyl)methylamino)methyl)anthracene, a diene capable of chelating to metal ions, as demonstrated by the successful synthesis of (9,10-bis(((2-(dimethylamino)ethyl)methylamino)methyl)anthracene-N,N',N",N^<*>)dizinc tetrachloride.