α-Diketones in [4+2]Cycloadditions, Reactions of Dimethyl 2,3-Dioxosuccinate 
with Enol Ethers

Sustmann, Rainer; Felderhoff, Michael

doi:10.3987/COM-94-S103

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α-Diketones in [4+2]Cycloadditions, Reactions of Dimethyl 2,3-Dioxosuccinate with Enol Ethers

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Felderhoff, Michael
Institut fur Organische Chemie, Universitat Essen, D-45117 Essen, Germany;
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Sustmann, R., & Felderhoff, M. (1995). α-Diketones in [4+2]Cycloadditions, Reactions of Dimethyl 2,3-Dioxosuccinate with Enol Ethers. Heterocycles, 40(2), 1027-1034. doi:10.3987/COM-94-S103.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-1DB9-8

Abstract

Dimethyl 2,3-dioxosuccinate (1) undergoes cycloaddition with enol ethers. Dihydrodioxine derivates, products of [4+2] cycloaddition, are formed with tetraethoxyethylene and E-1,2-dimethoxyethylene. The stereospecificity of the reaction of 1 with E-1,2-dimethoxyethylene suggests a concerted mechanism for this cycloaddition. The polarized double bond of ethyl vinyl ether reacts with 1 to give 4,5-dihydro-2,3-dimethoxycarbonyl-2,3-epoxy-5-ethoxyfuran in a hitherto unknown reaction of 1,2-diketones.