Water-soluble N-oxyl compounds-mediated electrooxidation of alcohols in water: A prominent access to a totally closed system

Tetrahedron Letters

Volumn 46, Issue 52, 2005, Pages 8975-8979

  Kubota, Jun ^a   Shimizu, Yusuke ^a   Mitsudo, Koichi ^a   Tanaka, Hideo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Alcohols; Aqueous solution; Electrooxidation; N Oxyl compounds; Water soluble mediators

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL GROUP; KETONE DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; BROMINATION; ELECTROLYSIS; OXIDATION;

EID: 28244484689     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.114     Document Type: Article

References (25)

1. K.J. Dignam, A.F. Hegarty, and P.L. Quain J. Org. Chem. 43 1978 388
2. D.C. Rideout, and R. Breslow J. Am. Chem. Soc. 102 1980 7816
3. S.D. Larsen, and P.A. Grieco J. Am. Chem. Soc. 107 1985 1768
4. A. Lubineau J. Org. Chem. 51 1986 2142
5. C.-J. Li Chem. Rev. 93 1993 2023
6. C.-J. Li, and T.-H. Chan Organic Reactions in Aqueous Media 1997 John Wiley & Sons New York
7. P.A. Grieco Organic Synthesis in Water 1998 Blackie Academic & Professional London
8. T. Hashizume, K. Yonehara, K. Ohe, and S. Uemura J. Org. Chem. 65 2000 5197
9. S. Kobayashi, T. Wakabayashi, S. Nakayama, and H. Oyamada Tetrahedron Lett. 38 1997 4559
10. S. Kobayashi, and K. Manabe Acc. Chem. Res. 35 2002 209
11. Electrooxidation of alcohols in homogeneous aqueous solution has been reported: T. Shono, Y. Matsumura, J. Hayashi, and M. Mizoguchi Tetrahedron Lett. 20 1979 165
12. B.A. Moyer, M.S. Thompson, and T.J. Meyer J. Am. Chem. Soc. 102 1980 2310
13. H. Tanaka, Y. Kawakami, K. Goto, and M. Kuroboshi Tetrahedron Lett. 42 2001 445
14. H. Tanaka, J. Kubota, S. Itogawa, T. Ido, M. Kuroboshi, K. Shimamura, and T. Uchida Synlett 2003 951
15. H. Tanaka, J. Kubota, S. Miyahara, and M. Kuroboshi Bull. Chem. Soc. Jpn. 78 2005 1677
16. Electrooxidation of alcohols using polymeric mediator has been reported: J. Yoshida, R. Nakai, and N. Kawabata J. Org. Chem. 45 1980 5269
17. In the previous papers, some kinds of water soluble N-oxyl compounds having (1) carboxylate, (2) ammonium, and (3) sulfonate units have been synthesized and used for spin labeling, radical polymerization, electron spin resonance, dynamic nuclear polarization in biological fluids, etc. (1): J.F.W. Keanes, and S. Pou J. Org. Chem. 54 1989 2417
18. K. Hideg, and L. Lex J. Chem. Soc., Perkin Trans. 1 1987 1117
19. W. Huang, B. Charleux, R. Chiarelli, L. Marx, A. Rassat, and J.-P. Vairon Macromol. Chem. Phys. 203 2002 1715
20. D.A. Reid, S.E. Bottle, and A.S. Micallef Chem. Commun. 1998 1907
21. D.A. Reid, S.E. Bottle, and A.S. Micallef Chem. Commun. 1998 1907
22. W. Huang, B. Charleux, R. Chiarelli, L. Marx, A. Rassat, and J.-P. Vairon Macromol. Chem. Phys. 203 2002 1715
23. L. Marx, and A. Rassat Chem. Commun. 2002 632
24. T. Inokuchi, S. Matsumoto, and S. Torii J. Org. Chem. 56 1991 2416
25. M. Kuroboshi, H. Yoshihisa, M.N. Cortona, Y. Kawakami, Z. Gao, and H. Tanaka Tetrahedron Lett. 41 2000 8131