Oxidation of primary and secondary alcohols by 4-acetylamino-2,2,6,6- tetramethylpiperidine-1-oxoammonium tetrafluoroborate in aqueous media

Arkivoc

Volumn 2011, Issue 5, 2011, Pages 23-33

  Mamros, Audrey N ^a   Sharrow, Phillip R ^b   Weller, William E ^a   Luderer, Mark R ^c   Fair, Justin D ^b   Pazehoski, Kristina O ^a   Luderer, Matthew R ^a  

^a University of Pittsburgh   (United States)

^b INDIANA UNIVERSITY OF PENNSYLVANIA   (United States)

^c UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

Aqueous organic chemistry; Oxidation; Oxoammonium salt

Indexed keywords

EID: 79955393341     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0012.504     Document Type: Article

References (30)

1. For a recent review, see Merbouh, N.; Bobbitt, J. M.; Brückner, C Org Prep. & Proc. Int. 2004, 36, 1
2. For select preparations of various oxoammonium salts, see (a) Zhdanov, R. I; Golubev, V. A.; Rozantsev, É. G. Izv. Akad Nauk USSR, Ser. Khim. 1970, 1, 188;
3. Chem. Abstr. 1970, 72, 111227.
4. (b) Golubev V. A., Zhadov R. I, Rozantsev E. G Izv. Akad Nauk USSR, Ser. Khim. 1970, 1, 186
5. Chem. Abstr. 1970, 72, 111229.
6. (c) Golubev, V. A.; Zhdanov, R I; Gida, V. M.; Rozantsev, E. G. Izv. Akad Nauk USSR, Ser. Khim. 1971, 4, 768;
7. Chem. Abstr. 1971, 75, 63571.
8. (d) Kagiya T., Komuro C., Sakano K., Nishimoto S. Chem. Lett. 1983, 365.
9. (e) Miyazawa T., Endo T., Shiihashi S., Okawara M. J. Org. Chem. 1985, 50, 1332.
10. (f) Bobbitt J. M. J. Org. Chem. 1998, 63, 9367.
11. For select oxidations, see ref 2f. (a) Bobbitt, J. M.; Flores M. C L. Heterocycles 1988, 27, 509.
12. (b) Ma, Z.; Bobbitt, J. M. J. Org Chem. 1991, 56, 6110.
13. (c) de Nooy A. E J. Besemer A. C. van Bekkum H. Synthesis 1996, 1153.
14. (d) Kernag, C A.; Bobbitt, J. M.; McGrath, D. V. J. Tetrahedron Lett. 1999, 40, 1635.
15. (a) Bobbitt, J. M. Chem. Eng News 1999, 77, 6.
16. (b) Molecules 1999, 4, M102.
17. Bobbitt, J. M.; Merbough, N. Organic Syntheses; Wiley: New York, 2005, Vol. 82; p 80.
18. For recent reviews, see (a) Li, C.-J.; Chen, L. Chem. Soc Rev. 2006, 1, 68.
19. (b) Minikata S., Komatsu M. Chem. Rev. 2009, 109, 711.
20. (c) Chanda, A; Foken, V. V. Chem. Rev. 2009, 109, 724
21. Breslow, R Acc Chem. Res. 2004, 37, 471.
22. Fair, J. D.; Kormos, C M. J. Chromatog A 2008, 1211, 49.
23. Coleman, G. H.; Honeywell, G. E. Organic Syntheses; Wiley: New York, 1959; Vol. 2, p 89.
24. Buramoy, A.; Markowitsch-Buramoy, I. J. Chem. Soc 1936, 36.
25. Brown, H. C.; McFarlin, R. F. J. Am. Chem. Soc 1956, 78, 252.
26. Drake, N. L.; Allen, P. Organic Syntheses; Wiley: New York, 1941; Coll. Vol. 1, p 77.
27. Claisen, L. Chem. Ber. 1877, 10, 429.
28. Marvel, C S.; Sperry, W. M. Organic Syntheses; Wiley: New York, 1941; Coll. Vol. 1, p 95.
29. Clark, H. T.; Dreger, E. E. Organic Syntheses; Wiley: New York, 1941; Coll. Vol. 1, p 87.
30. Ritter, J. J. J. Org. Chem. 1933, 55, 3322.