SWITCHING SELECTIVITY IN O-BENZOQUINONE CYCLOADDITIONS

Authors
ALTALIB M GERSTENBERGER I JONES PG WINTERFELDT E
Citation
M. Altalib et al., SWITCHING SELECTIVITY IN O-BENZOQUINONE CYCLOADDITIONS, Liebigs Annalen, (5), 1997, pp. 893-895
Citations number
7
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
5
Year of publication
1997
Pages
893 - 895
Database
ISI
SICI code
0947-3440(1997):5<893:SSIOC>2.0.ZU;2-I
Abstract
Whereas m-methoxy-o-benzoquinone 6, like other unsaturated ketones, op erates as a dienophile in Diels-Alder cycloadditions, the correspondin g methyl derivative 7a behaves as an electron-poor 4 pi-system under e xactly the same conditions. With the nonsymmetric cyclopentadiene 2 (X = MeO), adduct 9a is formed with excellent chemoselectivity, face-sel ectivity, and regioselectivity.