Abstract
Using a recently disclosed modification to the dimethyldioxirane method we have synthesized four arene monooxides and one trioxide in good to excellent yield. The X-ray crystal structures have been determined for all of these compounds. In the case of the chrysene trioxide the X-ray determination reveals that the structure is bent out of the plane.
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REFERENCES
Murray, R. W.; Singh, M.; Rath, N. P. Carcinogenesis 1999 20, 147. (b) Murray, R. W.; Singh, M.; Rath, N. P. Polycyclic Aromatic Compounds, 1999 13, 139.
Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985 50, 2847. (b) Singh, M.; Murray, R. W. J. Org. Chem. 1992 57, 4263. (c) Murray, R. W.; Singh, M. Org. Synth. 1996 74, (d) Adam, W.; Hadjiarapoglou, L.; Bialas, J. Chem. Ber. 1991 124, 2377.
Glusker, J. P.; Zacharias, D. E.; Carrell, H. L.; Fu, P. P.; Harvey, R. G. Cancer Res. 1976 36, 3951. (b) Glusker, J. P.; Carrell, H. L.; Zacharias, D. E.; Harvey, R. G. Cancer Biochem. Biophys. 1974 1, 43.
Kuroda, K.; Neidle, S. Carcinogenesis 1983 4, 217.
Glusker, J. P. In Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; ACS Symposium Series, American Chemical Society,; Washington, D.C., 1985; Vol. 283, p. 125. (b) Klein, C. L.; Stevens, C. D.; Acta Crystallogr., Sect. C, 1984 40, 315.
Murray, R. W.; Singh, M.; Rath, N. P. Tetrahedron Lett. 1996 37, 8671.
Boyland, E.; Sims, P. Int. J. Cancer 1967 2, 500.
Ishikawa, K.; Charles, H. C.; Griffin, G. W. Tetrahedron Lett. 1977 427.
Krishnan, S.; Kuhn, D. G.; Hamilton, G. A. Tetrahedron Lett. 1977 1369.
Krishnan, S.; Kuhn, D. G.; Hamilton, G. A. J. Am. Chem. Soc. 1977 99, 8121.
Harvey, R. G.; Goh, S.; Cortez, C. J. Am. Chem. Soc. 1975 97, 3466.
Van Duuren, B. L.; Witz, G.; Agarwal, S. J. Org. Chem. 1974 39, 1032.
Jeyaraman, R. J.; Murray, R. W. J. Am. Chem. Soc. 1984, 106 2462.
Murray, R. W.; Jeyaraman, R. J. In Polynuclear Aromatic Hydrocarbons: Tenth International Symposium on a Decade of Progress; Cooke, M. W.; Dennis, A. J., Eds.; Battelle Press, Columbus, Ohio 1985; p. 595.
Murray, R. W.; Rajadhyaksha, S. N.; Jeyaraman, R. Polycyclic Arom. Compounds 1990 1, 213.
Murray, R. W.; Pillay, M. K.; Snelson, M. J. in Polynuclear Aromatic Hydrocarbons: Measurements, Means, and Metabolism; Cooke, M. W.; Loening, K.; Merritt, J. Eds.; Battelle Press, Columbus, Ohio 1991; p. 615.
Murray, R. W.; Banavali, R. In Polynuclear Aromatic Hydrocarbons; Eighth International Symposium on Mechanisms, Methods, and Metabolism; Cooke, M. W.; Dennis, A. J. Eds.; Battelle Press, Columbus, Ohio 1983; p. 925.
Wood, A. W.; Levin, W.; Thakker, D. R.; Yagi, H.; Chang, R. L.; Ryan, D. E. Thomas, P. E.; Dansette, P. M.; Whittaker, N.; Turujman, S.; Lehr, R. E.; Kumar, S.; Jerina, D. M.; Conney, A. H. J. Biol. Chem. 1979, 254 4408
Lee, H.; Shayamasunder, N.; Harvey, R. G. J. Org. Chem. 1981 46, 2889.
Fronczek, F. R.; Keifer, G. E.; Newkome, G. R.; Griffin, G. W. Acta Crystallog., Sect. C, 1990 46, 2214.
Fabris, F.; Sbrogio, F.; De Lucchi, O.; Delogu, G.; Fabbri, D.; Valle, G. Gazz. Chim. Ital. 1997 127, 393.
Charles, C. H.; Baker, R. J.; Trefonas, L. M.; Griffin, G. W. J. Chem. Soc., Chem. Comm. 1980 1075.
Mohler, D. L.; Vollhardt, K. P. C.; Wolff, S. Angew. Chem. Int. Ed. Engl. 1995 34, 563.
Vogel, E.; Breuer, A.; Sommerfeld, C.-D.; Davis, R. E.; Liu, L.-K. Angew. Chem. Int. Ed. Engl. 1977 16, 1476.
Prout, P.; Smith, A. D.; Daub, G.; Zacharias, D. E.; Glusker, J. P. Carcinogenesis 1982 13, 1775.
Afshar, C. E.; Carrell, J. C.; Carrell, H. L.; Harvey, R. G.; Kiselyov, A. S.; Amin, S.; Glusker, J. P. Carcinogenesis 1996 17, 2507.
Carrell, J. C.; Carrell, T. G.; Carrell, H. L.; Prout, K.; Glusker, J. P. Carcinogenesis 1997 18, 415–422.
Flack, H. D. Acta Cryst. 1983 A39, 876.
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Murray, R.W., Singh, M. & Rath, N.P. X-ray Crystal Structures of Some Arene Oxides. Structural Chemistry 10, 419–427 (1999). https://doi.org/10.1023/A:1022475005317
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DOI: https://doi.org/10.1023/A:1022475005317