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Results and Discussion: Synthesis of 4,5-Benzoxepin for Comparative two electron oxidation reactions with Cerium Ammonium Nitrate and Cytochrome P450 Ryan W. Fitzgerald, Noah A. Cote, Arthur Greenberg rwj9@wildcats.unh.edu, Department of Chemistry, University of New Hampshire, Durham, NH 4/15/2018 Introduction: Benzene is a known carcinogen and dangerous chemical used in industry. Knowledge of the mechanistic pathways which potential toxins break down in the body is useful to prevent illnesses and help those ailing presently. Oxepin derivatives are useful models in investigating the ring opening mechanism of oxepin as seen in benzene metabolism. 4,5-Benzoxepin is a suitable substrate for use in enzymatic oxidation studies with cytochrome P450. This project focuses on synthesizing 4,5-benzoxepin and other model oxepins for use in enzymatic reactions by the Greenberg research group at UNH to establish the current metabolic pathway of benzene.3 Scheme 1. Metabolic routes of benzene in vivo. Scheme 3. Synthetic Route to 4,5-Benzoxepin 5 and dimer 6. Reactions with CAN were performed on 4,5-benzoxepin 5 yielding tentative products 6 with no 5 remaining. 1H NMR was used to characterize crude and pure products. Figure 1. 1H NMR of purified 6. Table 1. Enzymatic Protocol used with 4,5-benzoxepin. Synthesize a 2,3-benzoxepin and a benzodimer derivative. Explore enzyme reactions with new model oxepins. Attempt to grow crystals of the potential dimer to validate its structure further. The organic synthesis of 4,5-benzoxepin 5 was completed and improved. Enzymatic studies using benzene and 4,5-benzoxepin were finished. Preliminary results indicate that benzene can go through both epoxidation and two consecutive one electron oxidation mechanisms. The true structure of 6 remains unidentified and will require further analysis with GC-MS and X-ray crystal structure. The Greenberg research group, Sower research group, and UNH chemistry department are gratefully acknowledged. Vogel, E., Gunther, H., Angew. Chem. Int. Ed. 1967, 6, 385-476 Davies, S. G., Whitham, G. H., J. Chem. Soc. Perkin Trans. I, 1977, 1346-1347 Morgan, J., Greenberg, A., J. Org. Chem. 2010, 75, 4761-4768 Greenberg, A., et. al., Structural Chemistry, 1998, 9(3), 223-236 Nauduri, D., Greenberg, A., Tetrahedron Letters, 2004, 45, 4789-4793 Paquette, L. A., Barrett, J. H., Org. Synth. 1969, 49, 62. Rabideau, Peter W., Burkholder, E., J. Org Chem. 1978, 43, 4283-4288 Enzyme Substrate [Substrate] [Enzyme] NADPH MgCl2 2E1 4,5-benzoxepin 300 μM 50 pmol/mL 1.0 mM 3.3 mM 1A2 35 pmol/mL 3A4 35 pmol/mL pHLM 0.5 mg/mL Future Work: Conclusions: Results and Discussion: Acknowledgements: Experimental Work: References: Scheme 2. Alternative Synthetic Route to 4,5-Benzoxepin 5 and dimer 6.