Monday, 26 June 2006
Ponderosa (poster/exhibit) (John Ascuaga’s Nugget Casino Resort)
61

The taming of the Scholl

Charles R. Robertson, Jiří Kroulík, Cameron L. Hilton, Justin D. Korinek, Lisa M. Gortari, Pawel Rempala, and Benjamin T. King. University of Nevada, Reno, Reno, NV

Oxidative cyclization of polyphenylenes to fused polycyclic aromatic hydrocarbons (PAHs) has recently been investigated in our group. Electronic and structural properties of PAHs are theorized to be similar in nature to nanotubes, yet they are more synthetically accessible. We have undertaken the synthesis of substituted o-terphenyls (-OMe, -OH, -Br, -t-Bu), o-quaterphenyl, and o quinquephenyl. Subsequent Scholl oxidation gave products that were dependent on position of the substituents. Unsubstituted o-terphenyl gave rise to triphenylene, via intramolecular C-C bond formation, and a mixture of oligomers, by way of intermolecular C-C bond formations. In the substituted terphenyls, the outcome of the Scholl reaction was directed by the substituent, leading to predictable products. In this sense, we have reaffirmed the "slippery slope" mechanism for the Scholl reaction and found that bonds are formed in a classic electrophilic aromatic substitution manner.


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