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

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.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-1DB9-8 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-1DBA-6
Genre: Journal Article

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 Creators:
Sustmann, Rainer1, Author
Felderhoff, Michael1, 2, Author           
Affiliations:
1Institut fur Organische Chemie, Universitat Essen, D-45117 Essen, Germany, ou_persistent22              
2Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445589              

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 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.

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Language(s): eng - English
 Dates: 1995
 Publication Status: Issued
 Pages: -
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.3987/COM-94-S103
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Title: Heterocycles
Source Genre: Journal
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Publ. Info: Sendai, Japan : Elsevier
Pages: - Volume / Issue: 40 (2) Sequence Number: - Start / End Page: 1027 - 1034 Identifier: ISSN: 0385-5414
CoNE: https://pure.mpg.de/cone/journals/resource/954925528872