Issue 23, 1996

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

Abstract

The Ito–Saegusa method has been used to generate benzofuran-2,3-quinodimethane 10 from the corresponding sily 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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1996, 2827-2832

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

S. B. Bedford, M. J. Begley, P. Cornwall, J. P. Foreman and D. W. Knight, J. Chem. Soc., Perkin Trans. 1, 1996, 2827 DOI: 10.1039/P19960002827

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