Jessica Morgan - Insights into the Formation and Isomerization of the Benzene Metabolite Muconaldehyde and Related Molecules: Comparison of Computational and Experimental Studies of Simple, Benzo-Annelated, and Bridged 2,3-Epoxyoxepins

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  Publication Details (including relevant citation   information):

  Morgan, J., Greenberg, A. J. Org. Chem.,   2010, 75 (14), pp 4761–4768


  2,8-Dioxabicyclo[5.1.0]octa-3,5-diene (“2,3-epoxyoxepin”) has   been postulated as an intermediate in ring-opening metabolism of   benzene. Density functional theory (B3LYP/6-31G*) is employed to   study the activation and reaction energies for ring-opening   isomerization of 2,3-epoxyoxepin, its 4,5-benzo derivative, and   its 3,6-hexamethylene derivative. The results are compared with   published experimental data. The markedly different fates of   these three molecules suggest a means for testing the postulated   metabolic pathway.

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