Bismuth triflate catalyzed Friedel-Crafts acylations of sydnones

ORGN 144

Kenneth Turnbull, kenneth.turnbull@wright.edu, Department of Chemistry, Wright State University, Dayton, OH 45435 and Jennifer A. Fisher, fisher.79@wright.edu, Chemistry Department, Wright State University, 3640 Colonel Glenn Highway, Dayton, OH 45435.
Friedel-Crafts acylations on the 4 position of the sydnone ring have been achieved in high yields using 4 equivalents of various alkyl anhydrides, 25 mol % of bismuth triflate and lithium perchlorate in anhydrous acetonitrile at 95 C. Various para-substituted phenyl sydnones with different electron withdrawing and electron donating substituents were used to explore the effect of the attachment on the reaction time and yields of the acylation with acetic anhydride. Additionally, four other alkyl anhydrides were used to test their utility with phenyl sydnone. The scope of the reaction will be discussed.

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005