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

…, MJ Begley, P Cornwall, JP Foreman…

Index: Bedford, Simon B.; Begley, Michael J.; Cornwall, Philip; Foreman, Joel P.; Knight, David W. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 23 p. 2827 - 2832

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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.