Catalytic Epoxidation of Alkenes with Oxone. 2. Flupro Ketones

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8288-8289

  Denmark, Scott E ^a   Wu, Zhicai ^a   Crudden, Cathleen M ^a,b   Matsuhashi, Hayao ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001074226     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971781y     Document Type: Article

References (32)

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2. For reviews of dioxirane chemistry see: (a) Adam, W.; Curci, R.; Edwards, J. O Acc. Chem. Res. 1989, 22, 205. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187. Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxide; Ando, W., Ed.; J. Wiley & Sons: New York, 1992; Chapter 4. (e) Adam, W.; Hadjiarapoglou, L. P. In Topics in Current Chemistry; Springer-Verlag: Berlin, 1993; Vol. 164; p 45.
3. For reviews of dioxirane chemistry see: (a) Adam, W.; Curci, R.; Edwards, J. O Acc. Chem. Res. 1989, 22, 205. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187. Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxide; Ando, W., Ed.; J. Wiley & Sons: New York, 1992; Chapter 4. (e) Adam, W.; Hadjiarapoglou, L. P. In Topics in Current Chemistry; Springer-Verlag: Berlin, 1993; Vol. 164; p 45.
4. For reviews of dioxirane chemistry see: (a) Adam, W.; Curci, R.; Edwards, J. O Acc. Chem. Res. 1989, 22, 205. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187. Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, 1990; Vol. 2, Chapter 1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxide; Ando, W., Ed.; J. Wiley & Sons: New York, 1992; Chapter 4. (e) Adam, W.; Hadjiarapoglou, L. P. In Topics in Current Chemistry; Springer-Verlag: Berlin, 1993; Vol. 164; p 45.
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20. The application of this concept to more structurally complex ketones failed due to the choice of ring size and steric congestion surrounding the carbonyl group, (a) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
21. The application of this concept to more structurally complex ketones failed due to the choice of ring size and steric congestion surrounding the carbonyl group, (a) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
22. The preparation and full characterization of all new fluoro ketones are provided as Supporting Information.
23. (a) 10 mol % of ketone 4b gave only 6.3% conversion of (E)-5 to 6 after 24 h.
24. (b) Yang has also shown that in monophasic systems 1,1-1-trifluoromethyl ketones are not catalytically active. Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887.
25. 2O (1.5/1), 0 °C, 24 h.
26. Determined by GC. The lactone 12 produced under biphasic epoxidation conditions employing 1 equiv of 8 was isolated and fully characterized.
27. For a discussion of the chemistry of 2-halpcyclohexanones see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; pp 731-733.
28. (a) Linderman, R. J.; Jamois, E. A. J. Fluorine Chem. 1991, 53, 79.
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30. 3OD at 0.1 M. Both methanol adducts could be observed.
31. Allinger, N. L.; Blatter, H. M. J. Org. Chem. 1962, 27, 1523.
32. - was assured by single crystallographic analysis of the bromocamphorsulfonic acid salt of the methylation precursor.