Tungsten-mediated stereo- and regioselective additions to phenol

ORGN 380

Michael A. Todd, mat4h@virginia.edu1, Melissa L. Grachan, grachan@fas.harvard.edu2, Michal Sabat, ms5c@virginia.edu1, and W. Dean Harman1. (1) Department of Chemistry, University of Virginia, Charlottesville, VA 22903, (2) Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA 02138
Dihapto coordination of arenes to the p-basic metal fragment {TpW(NO)(PMe3)} effectively removes the 5,6 double bond of the arene. Coordination with phenol causes the ligand to tautomerize to a 2H-enone, which drastically alters its reactivity. The phenol complex will react with Michael acceptors and alkyl halides to form alkylated enones with a high degree of stereo- and regioselectivity. Also this complex will undergo aldol condensations with aldehydes to form o-quinone methides.

 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005