Dianion of tetrabenzo[5.7]fulvalene: The study of the aromaticity/antiaromaticity continuum via dianions

ORGN 104

Ashley Mynar, ashley.mynar@trinity.edu, Nancy S. Mills, nmills@trinity.edu, and Abraham Yousef, abraham.yousef@trinity.edu. Department of Chemistry, Trinity University, One Trinity Place, San Antonio, TX 78212-7200
Oxidation of tetrabenzo [5.5] fulvalene gives an antiaromatic dication while reduction gives the corresponding aromatic dianion, establishing a continuum from aromaticity to antiaromaticity, as shown below.

 

           

            We report the extension of this continuum to dications and dianions of tetrabenzo [5.7] fulvalene, as shown below.

            Dianions were prepared via reduction using lithium metal and characterized by NMR spectroscopy.  The results were compared to calculated values of aromaticity/ antiaromaticity such as nucleus independent chemical shifts (NICS) and magnetic susceptibility exaltation.  This data demonstrates that the dianion behaves as an aromatic system bonded to an antiaromatic system.

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006