Divergent Pathways in the Reaction of Hexamethylbenzene with Dimethyldioxirane

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8794-8799

  Murray, Robert W ^a   Singh, Megh ^a   Rath, Nigam ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344935543     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971339f     Document Type: Article

References (42)

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2. Portions of this work were published in preliminary form: Murray, R. W.; Singh, M., Rath, N. J. Org. Chem. 1996, 61, 7660.
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18. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
19. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
20. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
21. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
22. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
23. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
24. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
25. For reviews of dioxirane chemistry see: (a) Murray, R. W. Chem. Rev. (Washington, D.C.) 1989, 89, 1187. (b) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; J. Wiley and Sons: New York, 1992; Chapter 4. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (e) Adam, W.; Hadjiarapoglou, L. P. Top. Curr. Chem. 1993, 49, 2227. (f) Curci, R.; Dinoi, A.; Rubino, M. F. Pure and Appl. Chem. 1995, 67, 811. (g) Murray, R. W.; Singh, M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, Chapter 1.14, p 429. (h) Clennan, E. L. Trends Org. Chem. 1995, 5, 231.
26. For reviews and monographs on oxepin chemistry see: (a) Vogel, E.; Gunther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385. (b) Boyd, D. R.; Jerina, D. M. Small Ring Heterocycles, Part III. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; J. Wiley and Sons: New York, 1985; Vol. 42, p 197. Shirwaiker, G. S.; Bhatt, M. V. in Advances in Heterocylic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL; 1984; Vol. 37, p 67. Boyd, D. R. In Comprehensive Heterocylic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, Chapter 5.17, p 547. (e) Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, 1991, p 276. (f) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 289.
27. For reviews and monographs on oxepin chemistry see: (a) Vogel, E.; Gunther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385. (b) Boyd, D. R.; Jerina, D. M. Small Ring Heterocycles, Part III. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; J. Wiley and Sons: New York, 1985; Vol. 42, p 197. Shirwaiker, G. S.; Bhatt, M. V. in Advances in Heterocylic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL; 1984; Vol. 37, p 67. Boyd, D. R. In Comprehensive Heterocylic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, Chapter 5.17, p 547. (e) Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, 1991, p 276. (f) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 289.
28. For reviews and monographs on oxepin chemistry see: (a) Vogel, E.; Gunther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385. (b) Boyd, D. R.; Jerina, D. M. Small Ring Heterocycles, Part III. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; J. Wiley and Sons: New York, 1985; Vol. 42, p 197. Shirwaiker, G. S.; Bhatt, M. V. in Advances in Heterocylic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL; 1984; Vol. 37, p 67. Boyd, D. R. In Comprehensive Heterocylic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, Chapter 5.17, p 547. (e) Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, 1991, p 276. (f) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 289.
29. For reviews and monographs on oxepin chemistry see: (a) Vogel, E.; Gunther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385. (b) Boyd, D. R.; Jerina, D. M. Small Ring Heterocycles, Part III. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; J. Wiley and Sons: New York, 1985; Vol. 42, p 197. Shirwaiker, G. S.; Bhatt, M. V. in Advances in Heterocylic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL; 1984; Vol. 37, p 67. Boyd, D. R. In Comprehensive Heterocylic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, Chapter 5.17, p 547. (e) Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, 1991, p 276. (f) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 289.
30. For reviews and monographs on oxepin chemistry see: (a) Vogel, E.; Gunther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385. (b) Boyd, D. R.; Jerina, D. M. Small Ring Heterocycles, Part III. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; J. Wiley and Sons: New York, 1985; Vol. 42, p 197. Shirwaiker, G. S.; Bhatt, M. V. in Advances in Heterocylic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL; 1984; Vol. 37, p 67. Boyd, D. R. In Comprehensive Heterocylic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, Chapter 5.17, p 547. (e) Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, 1991, p 276. (f) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 289.
31. For reviews and monographs on oxepin chemistry see: (a) Vogel, E.; Gunther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385. (b) Boyd, D. R.; Jerina, D. M. Small Ring Heterocycles, Part III. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; J. Wiley and Sons: New York, 1985; Vol. 42, p 197. Shirwaiker, G. S.; Bhatt, M. V. in Advances in Heterocylic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL; 1984; Vol. 37, p 67. Boyd, D. R. In Comprehensive Heterocylic Chemistry; Katritzky, A. R., Rees, C. W., Lwowski, W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, Chapter 5.17, p 547. (e) Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, 1991, p 276. (f) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 289.
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