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Photooxygenation of 1,2-Diaryltetrahydrobenziimidazole and Crystal Structure of Its Product
Corresponding Author(s) : Xiaoyan Shi
Asian Journal of Chemistry,
Vol. 25 No. 3 (2013): Vol 25 Issue 3
Abstract
The reactions of 1-(4-methylsulfonylphenyl)-2-(2,5-chlorophenyl)tetrahydrobenziimidazole (1) with singlet oxygen has been investigated. Compound 1, from a initially formed 2,5-endoperoxide and the subsequence instable zwitterion intermediate, generated a dioxetane. The formed dioxetane through ring-opening and interior-ring electrophilic reaction and finally converted into a more stable seven-membered ring product which has not been reported before. The structure of the photooxygenation product was elucidated by X-ray analysis, H NMR, MS and elemental analysis. The compound 1,2-diaryltetrahydrobenziimidazole crystallizes in monoclinic, space group P2(1)/c with a = 18.533(4) (Å), a = 90(º); b = 7.7658(16) (Å), b = 91.96(3)(º); c = 14.203(3) (Å), g = 90(º); V = 2042.9(7) Å3, Z = 4, F(000) = 948, Dc = 1.474 (g cm-3), C20H18N2O4SCl2, Mr = 453.39 and μ = 0.444 mm-1.
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- R.Y.N. Ho, J.F. Liebman and J.S. Valentine, Overview of Energetics and Reactivity of Oxygen; In Active Oxygen in Chemistry, in eds.: C.S. Foote; J.S. Valentine, A. Greenberg and J. Liebman, Blackie Academic & Professional, Glasgow (1995).
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- H.H. Wasserman, M.S. Wolff, H. Ktiller, I. Aaito and J.E. Pickett, Tetrahedron, 9S, 191 (1981).
- T. Suzuki, M.D. Friesen and H. Ohshima, Bioorg. Med. Chem., 11, 2157 (2003).
- H.R. Shen, J.D. Spikes, C.J. Smith and J.J. Kopecek, Photochem. Photobiol. A, 130, 1 (2000).
- A. Boldyrev and H. Abe, Cell. Mol. Neurobiol., 19, 163 (1999).
- Au.V. Madison and S.A. Arch. Biochem. Biophys., 384, 133 (2000).
- H.S. Ryang and C.S. Foote, J. Am. Chem. Soc., 101, 6683 (1979).
- M.Y. Li, H. Liu and B.H. Zhong, Chin. J. Med. Chem., 16, 284 (2006)
References
R.Y.N. Ho, J.F. Liebman and J.S. Valentine, Overview of Energetics and Reactivity of Oxygen; In Active Oxygen in Chemistry, in eds.: C.S. Foote; J.S. Valentine, A. Greenberg and J. Liebman, Blackie Academic & Professional, Glasgow (1995).
E.L. Clennana and A. Pace, Tetrahedron, 61, 6665 (2005).
C. Sheu, P. Kang, S. Khan and C.S. Foote, J. Am. Chem. Soc., 124, 3905 (2002).
V.V. Agon, W.A. Bubb, A. Wright, C.L. Hawkins and M.J. Davies, Free Radic. Biol. Med., 40, 698 (2006).
H.H. Wasserman, M.S. Wolff, H. Ktiller, I. Aaito and J.E. Pickett, Tetrahedron, 9S, 191 (1981).
T. Suzuki, M.D. Friesen and H. Ohshima, Bioorg. Med. Chem., 11, 2157 (2003).
H.R. Shen, J.D. Spikes, C.J. Smith and J.J. Kopecek, Photochem. Photobiol. A, 130, 1 (2000).
A. Boldyrev and H. Abe, Cell. Mol. Neurobiol., 19, 163 (1999).
Au.V. Madison and S.A. Arch. Biochem. Biophys., 384, 133 (2000).
H.S. Ryang and C.S. Foote, J. Am. Chem. Soc., 101, 6683 (1979).
M.Y. Li, H. Liu and B.H. Zhong, Chin. J. Med. Chem., 16, 284 (2006)