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Synthesis 1996; 1996(1): 77-81
DOI: 10.1055/s-1996-4176
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The Generation of Anthra[2,3-c]furan via Aromatic-Ring Homologation of Naphtho[2,3-c]furan

Noah P.W. Tu, Judy C. Yip, Peter W. Dibble*
  • *Department of Chemistry, University of Lethbridge, Lethbridge Alberta T1K 3M4, Canada, Fax +1(403)3292057; E-mail DIBBLE@HG.ULETH.CA
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Publikationsdatum:
31. Dezember 2000 (online)

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Anthra[2,3-c]furan, a higher aromatic homologue of isobenzofuran, has been predicted to be a highly reactive polyene lacking any significant aromatic character despite being a 14 π-electron system. We have generated this previously inaccessible molecule by acid-catalyzed elimination of methanol from an acetal precursor, and have trapped it with several dienophiles. The overall reaction sequence describes an aromatic-ring homologenation of naphtho[2,3-c]furan to anthra[2,3-c]furan.

2-hydroxybutenolide is used to homologate naphtho[2,3-c]furan to anthra[2,3-c]furan.

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