Diels-Alder reactivity of a novel phenylsulfonylfuran

ORGN 694

John A. Milligan, milligj@allegheny.edu and S. Shaun Murphree, smurphre@allegheny.edu. Department of Chemistry, Allegheny College, 520 N. Main Street, Meadville, PA 16335

The Diels-Alder reactivity of the novel (phenylsulfonyl)ethenylfuran (1) is presented. The regiochemical outcome (furan-type cycloaddition to give bridged adducts of type 2 vs. exocyclic Diels-Alder to give fused bicyclic products of type 3) is discussed as a function of dienophile identity, as well as the presence and identity of a Lewis-acid catalyst.

 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009