Heiner, Thomas; Kozhushkov, Sergei I.; Noltemeyer, Mathias; Haumann, Thomas; Boese, Roland; de Meijere, Armin:
Intramolecular Diels-Alder reactions of furans with a merely strain-activated tetrasubstituted alkene: bicyclopropylidene.
1996
In: Tetrahedron (Tetrahedron), Jg. 52 (1996), Heft 37, S. 12185 - 12196
Artikel/Aufsatz in Zeitschrift / Fach: Chemie
Titel:
Intramolecular Diels-Alder reactions of furans with a merely strain-activated tetrasubstituted alkene: bicyclopropylidene.
Autor(in):
Heiner, Thomas; Kozhushkov, Sergei I.; Noltemeyer, Mathias; Haumann, Thomas; Boese, Roland im Online-Personal- und -Vorlesungsverzeichnis LSF anzeigen; de Meijere, Armin
Erscheinungsjahr
1996
Erschienen in:
Tetrahedron (Tetrahedron), Jg. 52 (1996), Heft 37, S. 12185 - 12196
ISSN

Abstract:

Bicyclopropylidene derivs., e.g., I (R = H, OMe), with furan moieties attached on tethers of various length and nature all undergo clean intramol. Diels-Alder reactions with complete endo-diastereoselectivities when heated to 70 - 130 DegC, under 10 kbar pressure. The reaction rates are at least as high or higher than those of analogously tethered methylenecyclopropane-furan derivs., e.g., II, in spite of the fact that the reactive double bond in bicyclopropylidene is tetrasubstituted and not activated by any electron withdrawing group.