Benzofuran synthesis via α-acylcarbonium ions

ORGN 554

Na Liu, nliu1@kent.edu and Robert J. Twieg, rtwieg@lci.kent.edu. Department of Chemistry, Kent State University, Kent, OH 44242
Benzofurans comprise an important class of heterocyclic compounds. Many benzofuran derivatives possess biological activity and have also recently been developed for electro-optic applications as two-photon singlet oxygen sensitizers and for electroluminescence. The reactions between dialkoxy and diaryl substituted benzoin derivatives and substituted phenols and naphthols to form benzofurans have been examined using SOCl2 or PPh3/CCl4 in a variety of solvents. A range of differently substituted furan monomers, dimers and trimers has been synthesized using this method. This reaction proceeds via an α-acylcarbenium ion intermediate so suitable substituents which can stabilize this intermediate are essential. The overall synthesis process for these benzofurans and the scope of the reaction will be discussed.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

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