Nitroxyl-Mediated Electrooxidation of Alcohols to Aldehydes and Ketones

Journal of the American Chemical Society

Volumn 105, Issue 13, 1983, Pages 4492-4494

  Semmelhack, M F ^a   Chou, Chuen S ^a   Cortes, David A ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845552369     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00351a070     Document Type: Article

References (24)

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2. Bromide anion: Shono, T.; Matsumura, Y.; Hayashi, J. Tetrahedron Lett. 1980, 21, 1867-1870.
3. Iodide anion: Shono, T.; Matsumura, Y.; Hayashi, J.; Mizoguchi, M. Tetrahedron Lett. 1979, 20, 164-168.
4. nitrate: Leonard, J. E.; Scholl, P. C.; Steckel, T. P.; Lentsch, S.E.; van de Mark M. R. Tetrahedron Lett. 1980, 21, 4695-4699.
5. Poly(4-vinylpyridine): Yoshida, J.-I.; Nakai, R.; Kawabata, N. J. Org. Chem. 1980, 45, 5269.
6. Golubev, V. A.; Rozantsev, E. G.; Neiman, M. B. Bull. Acad. Sci. USSR 1965, 1927-1936.
7. Cella, J. A.; Kelley, J. A.; Kenehan, E. F. Tetrahedron Lett. 1975, 2869-2872.
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12. This potential is well below that for electrooxidation of most common functional groups.
13. For a comprehensive list of redox potentials for organic compounds, see: Meites, L.; Zuman, P. “Electrochemical Data”; Wiley: New York, 1974; Part 1, Vol. A.
14. Golubev, V. A.; Rozantsev, E. G.; Neiman, M. B. Bull. Acad. Sci. USSR 1978, 1874-1881.
15. Celia, J. A.; Kelley, J. A.; Kenehan, E. F. J. Org. Chem. 1975, 40, 1860-1862.
16. Ganem, B. J. Org. Chem. 1975, 40, 1998-1999.
17. Celia, J. A.; McGrath, J. P.; Regen, S. L. Tetrahedron Lett. 1975, 4115-4118.
18. A value of 1630 cm-1 (KBr) was assigned to the N=0 stretch in the chloride salt: Atovmzan, L. O.; Golubev, V. A.; Golovina, N. I.; Klitskaya, G. A. Zh. Strukt. Khim. 1975, 16, 92.
19. The synthesis of dio. 4-7 follows that previously reported: Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310.
20. Catalytic oxidation using Pt02 and oxygen is an effective method for oxidation of primary alcohols in the presence of secondary. However, the process is not generally effective at producing simple aldehydes. Further oxidation to carboxylic acids or lactones is the most effective application, Heyns, K.; Paulsen, H. In “Newer Methods of Preparative Organic Chemistry”; Academic Press: New York, 1963; Vol. 2, pp. 303 ff. For specific recent applications in lactone synthesis, see:
21. Lansbury, P. T. Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964.
22. Kretchmer, A.; Thompson, W. J. J. Am. Chem. Soc. 1976, 98, 3379.
23. Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 3899.
24. A recent report describes an oxidation procedure that is effective for primary alcohols in the presence of secondary. A test of primary vs. allylic secondary was not included, the system requires stoichiometric amounts of the oxidizing agent tris(triphenylphosphine)trichlororuthenium(II). Tomioka, N.; Takai, K.; Oshima, K.; Nozak, H. Tetrahedron Lett. 1981, 22, 1605-1608.