Oxidation of organonitrogen compounds by the methyltrioxorhenium-hydrogen peroxide system

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 805-808

  Murray, Robert W ^a   Iyanar, Kaliappan ^a   Chen, Jianxin ^b   Wearing, James T ^b  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^b PAPRICAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NITROXIDE DERIVATIVE;

ARTICLE; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030047332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02326-7     Document Type: Article

References (24)

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5. b.) Adam, W.; Herrmann, W.A.; Lin, J.; Saha-Moller, C.R. J. Org. Chem. 1994, 59, 8281-8283.
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8. Yamazaki, S. Chem. Lett. 1995, 127-128.
9. For reviews of dioxirane chemistry see: a.) Murray, R.W. In Molecular Structure and Energetics. Unconventional Chemical Bonding (Vol 6); Liebman, J.F., Greenberg, A., Eds.; VCH Publishers, New York, 1988; pp 311-351. b.) Murray, R.W. Chem. Rev. 1989, 89, 1187-1201. c.) Curci, R. In Advances in Oxygenated Processes; Baumstark, A.L. Ed.; JAI Publishers, Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59. d.) Adam, W., Hadjiarapoglou, L.P., Curci, R., Mello R. In Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992; Chapter 4, pp 195-219. e.) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211. f.) Curci, R.; Dinoi, A.; Rubino, M.F. Pure and Appl. Chem. 1995, 67, 811-822.
10. For reviews of dioxirane chemistry see: a.) Murray, R.W. In Molecular Structure and Energetics. Unconventional Chemical Bonding (Vol 6); Liebman, J.F., Greenberg, A., Eds.; VCH Publishers, New York, 1988; pp 311-351. b.) Murray, R.W. Chem. Rev. 1989, 89, 1187-1201. c.) Curci, R. In Advances in Oxygenated Processes; Baumstark, A.L. Ed.; JAI Publishers, Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59. d.) Adam, W., Hadjiarapoglou, L.P., Curci, R., Mello R. In Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992; Chapter 4, pp 195-219. e.) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211. f.) Curci, R.; Dinoi, A.; Rubino, M.F. Pure and Appl. Chem. 1995, 67, 811-822.
11. For reviews of dioxirane chemistry see: a.) Murray, R.W. In Molecular Structure and Energetics. Unconventional Chemical Bonding (Vol 6); Liebman, J.F., Greenberg, A., Eds.; VCH Publishers, New York, 1988; pp 311-351. b.) Murray, R.W. Chem. Rev. 1989, 89, 1187-1201. c.) Curci, R. In Advances in Oxygenated Processes; Baumstark, A.L. Ed.; JAI Publishers, Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59. d.) Adam, W., Hadjiarapoglou, L.P., Curci, R., Mello R. In Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992; Chapter 4, pp 195-219. e.) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211. f.) Curci, R.; Dinoi, A.; Rubino, M.F. Pure and Appl. Chem. 1995, 67, 811-822.
12. For reviews of dioxirane chemistry see: a.) Murray, R.W. In Molecular Structure and Energetics. Unconventional Chemical Bonding (Vol 6); Liebman, J.F., Greenberg, A., Eds.; VCH Publishers, New York, 1988; pp 311-351. b.) Murray, R.W. Chem. Rev. 1989, 89, 1187-1201. c.) Curci, R. In Advances in Oxygenated Processes; Baumstark, A.L. Ed.; JAI Publishers, Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59. d.) Adam, W., Hadjiarapoglou, L.P., Curci, R., Mello R. In Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992; Chapter 4, pp 195-219. e.) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211. f.) Curci, R.; Dinoi, A.; Rubino, M.F. Pure and Appl. Chem. 1995, 67, 811-822.
13. For reviews of dioxirane chemistry see: a.) Murray, R.W. In Molecular Structure and Energetics. Unconventional Chemical Bonding (Vol 6); Liebman, J.F., Greenberg, A., Eds.; VCH Publishers, New York, 1988; pp 311-351. b.) Murray, R.W. Chem. Rev. 1989, 89, 1187-1201. c.) Curci, R. In Advances in Oxygenated Processes; Baumstark, A.L. Ed.; JAI Publishers, Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59. d.) Adam, W., Hadjiarapoglou, L.P., Curci, R., Mello R. In Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992; Chapter 4, pp 195-219. e.) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211. f.) Curci, R.; Dinoi, A.; Rubino, M.F. Pure and Appl. Chem. 1995, 67, 811-822.
14. For reviews of dioxirane chemistry see: a.) Murray, R.W. In Molecular Structure and Energetics. Unconventional Chemical Bonding (Vol 6); Liebman, J.F., Greenberg, A., Eds.; VCH Publishers, New York, 1988; pp 311-351. b.) Murray, R.W. Chem. Rev. 1989, 89, 1187-1201. c.) Curci, R. In Advances in Oxygenated Processes; Baumstark, A.L. Ed.; JAI Publishers, Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59. d.) Adam, W., Hadjiarapoglou, L.P., Curci, R., Mello R. In Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992; Chapter 4, pp 195-219. e.) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211. f.) Curci, R.; Dinoi, A.; Rubino, M.F. Pure and Appl. Chem. 1995, 67, 811-822.
15. Herrmann, W.A.; Fischer, R.W.; Scherer, W.; Rauch, M.U. Angew. Chem. Int. Ed. Engl. 1993, 32, 1157-1160.
16. Yamazaki, S.; Espenson, J.H.; Huston, P. Inorg. Chem. 1993, 32, 4683-4687.
17. 2. Analyses of these solutions indicated that the reactions were very clean and contained products as shown in the Table. A control reaction with pyridine indicated that no oxide product is formed in the absence of the catalyst in the reaction time shown.
18. Murray, R.W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853.
19. Murray, R.W.; Mohan, L.; Jeyaraman, R. Tetrahedron Lett. 1986, 27, 2335-2336.
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22. Murray, R.W.; Singh, M. Synthetic Comm. 1989, 19(20), 3509-3522.
23. 14 In particular it had the same ESR spectrum as the authentic sample.
24. Keana, J.F.W.; Keana, S.B.; Beetham, D. J. Am. Chem. Soc. 1967, 89, 3055-3056.