Synthesis of halogenated azulenic ketones

CHED 487

Anna Blice-Baum, spyridis@jaguar1.usouthal.edu, Brittney Gros, bng501@jaguar1.usouthal.edu, and Greg T. Spyridis, spyridis@jaguar1.usouthal.edu. Department of Chemistry, University of South Alabama, Mobile, AL 36688
Azulene undergoes electrophilic aromatic substitution primarily at the 1 and 3 positions. Reaction with perfluorinated acid anhydrides and trichloroacetic anhydride occurs at room temperature without a Lewis acid catalyst. Consequently, we have adapted a literature procedure [Mathias, L. J.; Overberger, C. G. J. Org. Chem. 1980, 45, 1701] to synthesize several 1-substituted and 1,3-disubstituted azulenic ketones of the type 1 and 2.