AMBIENT-TEMPERATURE METHOD FOR THE GENERATION AND DIELS-ALDER TRAPPING OF BENZOFURAN-2,3-QUINODIMETHANE (2,3-DIMETHYLIDENE-2,3-DIHYDROBENZOFURAN)

Authors
BEDFORD SB BEGLEY MJ CORNWALL P FOREMAN JP KNIGHT DW
Citation
Sb. Bedford et al., AMBIENT-TEMPERATURE METHOD FOR THE GENERATION AND DIELS-ALDER TRAPPING OF BENZOFURAN-2,3-QUINODIMETHANE (2,3-DIMETHYLIDENE-2,3-DIHYDROBENZOFURAN), Journal of the Chemical Society. Perkin transactions. I, (23), 1996, pp. 2827-2832
Citations number
85
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
23
Year of publication
1996
Pages
2827 - 2832
Database
ISI
SICI code
0300-922X(1996):23<2827:AMFTGA>2.0.ZU;2-2
Abstract
The Ito-Saegusa method has been used to generate benzofuran-2,3-quinod imethane 10 from the corresponding silyl acetate 17b in solution at -4 degrees C. The intermediate reacts efficiently with a range of reacti ve Diels-Alder dienophiles with moderate to good levels of regioselect ion; the structure of the major diastereoisomer has been determined by X-ray analysis.