Ambient temperature method for the generation and Diels-Alder trapping of benzofuran-2,3-quinodimethane (2,3-dimethylidene-2,3-dihydrobenzofuran)

Simon B. Bedford, Michael J. Begley, Philip Cornwall, Joel P. Foreman, David W. Knight

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

The Ito-Saegusa method has been used to generate benzofuran-2,3-quinodimethane 10 from the corresponding silyl acetate 17b in solution at -4°C. The intermediate reacts efficiently with a range of reactive Diels-Alder dienophiles with moderate to good levels of regioselection; the structure of the major diastereoisomer has been determined by X-ray analysis.
Original languageEnglish
Pages (from-to)2827-2832
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 1
Volume23
DOIs
Publication statusPublished - 1996

Keywords

  • chemistry

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