Weiss Reaction

U. Weiss, J. M. Edwards, Tetrahedron Letters 1968, 4885.

Reaction of 1,2-dicarbonyl compounds with 3-oxoglutarates to yield cis-bicyclo[3.3.0]octane-3,7-dione or [n.3.3]propellanedione (n > 2) tetracarboxylates. Subsequent acid-catalyzed hydrolysis and decarboxylation yield the respective 2,4,6,8-unsubstituted diones:



Experimental procedure: S. H. Bertz et al., Org. Syn. coll. vol. VII, 50 (1990). Review of synthetic applications: A. K. Gupta et al., Tetrahedron 47, 3665-3710 (1991). Review: H.-U. Reissig, “The Weiss Reaction” in Organic Synthesis Highlights, J. Mulzer et al., Eds. (VCH, New York, 1991) pp 121-125.