Dioxygenation of Aromatic Compounds

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Professor Goff of the University of Iowa will attempt to catalyze the dioxygenation of aromatic compounds with support from the Inorganic, Bioinorganic, and Organometallic program. The attempt is motivated by the existence of metalloenzymes that perform this feat. Goff will investigate hemes, manganese porphyrins, and non-porphyrin iron and manganese compounds for their ability to catalyze the introduction of both atoms of an oxygen molecule across adjacent atoms of aromatic rings. He will use porphyrin compounds that are known to coordinate peroxide in a side-on configuration, and he will tune the reactivity by altering the substituents on the porphyrin periphery. Paramagnetic NMR will play an important role in assessing the effects of these substituents. Success in this endeavor would add a major new dimension to abiological oxidation chemistry. %%% Dioxygenases are naturally-occurring enzymes that catalyze reactions of molecular oxygen with aromatic organic compounds such that both oxygen atoms become bound to the organic product. Reactions of this type are unknown in synthetic chemistry, but are potentially of great value. A concerted effort to develop such reactivity will be conducted, and it will be guided by current insight regarding the bonding of O2 to certain metal-containing compounds. It is considered that by bonding to the metal center, the properties of O2 will be sufficiently altered that it will react as though a dioxygenase enzyme were present.