Synthesis of highly-substituted azulenes and polyazulenes. Transition metal-mediated coupling reactions of azulenyl halides, sulfonates, and azulenylmetal compounds

ORGN 377

Aimee L. Crombie, Kevin M. Shea, John L. Kane, and Rick L. Danheiser. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139

A ring expansion-annulation strategy has been developed which provides efficient access to highly-substituted azulenes including azulenyl halides, sulfonates, and azulenylmetal compounds beginning from readily available benzenes. These azulene annulation products participate in a variety of trasition metal-mediated coupling processes, including the Heck, Stille, Suzuki, and Negishi reactions. The application of this strategy to the synthesis of azulenes of interest in biology and materials science will also be described.

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions 8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster Division of Organic Chemistry The 226th ACS National Meeting, New York, NY, September 7-11, 2003