ON THE TENDENCY OF 1,2,3,6-TETRAHYDROBENZOCYCLOBUTENE-3,6-DIONES FOR UNDERGOING SITE-SELECTIVE DIELS-ALDER REACTIONS AT THE INTERNAL DOUBLE-BOND

Authors
ROTHENFLUH DF CRAIG DC PADDONROW MN
Citation
Df. Rothenfluh et al., ON THE TENDENCY OF 1,2,3,6-TETRAHYDROBENZOCYCLOBUTENE-3,6-DIONES FOR UNDERGOING SITE-SELECTIVE DIELS-ALDER REACTIONS AT THE INTERNAL DOUBLE-BOND, Tetrahedron letters, 36(7), 1995, pp. 1129-1132
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
7
Year of publication
1995
Pages
1129 - 1132
Database
ISI
SICI code
0040-4039(1995)36:7<1129:OTTO1F>2.0.ZU;2-O
Abstract
Diels-Alder reactions of cyclobutene-3,6-diones, 5 and 6 with dienes 7 - 10 gave predominantly adducts arising from attack of the diene at t he internal double bond of the diones. Ab initio MO calculations sugge st that the observed site selectivity of cyclobutene-3,6-diones is due to strain effects rather than to frontier orbital effects.