Synthesis of substituted 3-furan-2(5H)-ones via an anthracene Diels-Alder sequence |
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| Authors: | Simon Jones Ian Wilson |
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| Institution: | Department of Chemistry, Dainton Building, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK |
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| Abstract: | Deprotonation then electrophilic quench of the lactone derived from the Diels-Alder addition adduct of anthracene and maleic anhydride gave α-substituted lactones in good yield. Of particular note was the reaction with chlorotrimethylsilane which gave only the C-silylated product. Flash vacuum pyrolysis (FVP) of the alkylated products afforded 3-substituted furan-2(5H)-ones in good overall yield. |
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