Radical [n+1] annulations with sulfur dioxide

ORGN 191

Anna Tsimelzon, tsimelzon@yahoo.com, 745 S. Bernardo aven., #313, Sunnyvale, CA 94087 and Rebecca Braslau, braslau@chemistry.ucsc.edu, Department of Chemistry and Biochemistry, University of California, Santa Cruz, Thimann Laboratories, Santa Cruz, CA 95064.
A new methodology for [n+1] radical annulation using sulfur dioxide as a geminal radical acceptor/donor is presented. The reaction utilizes allylic sulfides as substrates. The reaction is performed at room temperature using light and diphenyl disulfide as the initiating system. This new methodology provides a novel route to the formation of 5, 6, and 7-membered cyclic sulfones in good to excellent yields under very mild conditions.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C301, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006