Formation of polycyclic scaffolds from tungsten-arene complexes

ORGN 594

Edward C. Lis Jr.1, William H. Myers2, and W Dean Harman1. (1) Department of Chemistry, University of Virginia, Charlottesville, VA 22904, (2) Department of Chemistry, University of Richmond
The pi-basic metal fragment {TpW(NO)(PMe3)} has been shown to bind anisole and 3-methyl anisole in a dihapto fashion. In the presence of a weak acid, Michael acceptors add readily to the 4-position of the dearomatized anisoles, resulting in a series of alkylated 4H-anisolium complexes, which have proven to be versatile intermediates in the formation of a variety of polycyclic systems. Herein, the synthesis of hexahydrochromenes, tetrahydronaphthalenes, and bicyclo[3.3.1]non-3-en-2-ones will be described.
 

Metal-Mediated Reactions and Syntheses
1:00 PM-4:20 PM, Wednesday, March 28, 2007 McCormick Place Lakeside -- Room E350, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007