Transferring oxygen atoms to difficult or "impossible" sites using HOF•CH3CN

ORGN 417

Shlomo Rozen, rozens@post.tau.ac.il, Elizabeta Amir, golanlis@post.tau.ac.il, Mira Carmeli, carmelim@post.tau.ac.il, and Tal Harel, talharel@post.tau.ac.il. School of Chemistry, Tel Aviv University, 69978 Tel Aviv, Israel
Among the thousands of papers devoted to oligothiophenes emphasizing their importance in organo-electronics, the family of All-S,S-dioxide-oligothiophenes is conspicuously missing despite theoretical predictions of its importance. This frustration is due to the fact that no convention oxidizer was able to transfer enough oxygen atoms to any oligothiophene higher than bithiophene. HOF•CH3CN, developed in our labs, is the only oxygen transfer agent which was successful in creating this family. This reagent was also instrumental in transferring episulfides to episulfones, in forming quinoxoline oxide derivatives and other oxygen containing compounds difficult or impossible to make with conventional oxygen transfer agents.

 

New Reactions and Methodology
1:00 PM-5:20 PM, Tuesday, 12 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006