Electrocatalytic oxidation of benzyl alcohol and 1-phenethyl alcohol by a decahydroquinolinyl-N-oxyl radical

Heterocycles

Volumn 50, Issue 1, 1999, Pages 79-82

  Kurashima, Futoshi ^a   Kashiwagi, Yoshitomo ^a   Kikuchi, Chikara ^a   Anzai, Jun Ichi ^a   Osa, Tetsuo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE; BENZALDEHYDE; BENZYL ALCOHOL; DECAHYDROQUINOLINE DERIVATIVE; PHENETHYL ALCOHOL; RADICAL; SILVER DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ELECTROCHEMICAL ANALYSIS; ELECTROLYSIS; OXIDATION; POTENTIOMETRY; REACTION ANALYSIS;

EID: 0032837955     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s(h)58     Document Type: Article

References (23)

1. M. F. Semmelhack, C. R. Schmid, D. A. Cortes, and C. S. Chou, J. Am. Chem. Soc., 1983, 105, 4492.
2. T. Endo, T. Miyazawa, S. Shiihashi, and M. Okawara, J. Am. Chem. Soc., 1984, 106, 3877; E. Yoshida, T. Takata, T. Endo, T. Ishizone, A. Hirao, and S. Nakahama, Chem. Lett., 1994, 1827.
3. T. Endo, T. Miyazawa, S. Shiihashi, and M. Okawara, J. Am. Chem. Soc., 1984, 106, 3877; E. Yoshida, T. Takata, T. Endo, T. Ishizone, A. Hirao, and S. Nakahama, Chem. Lett., 1994, 1827.
4. (a) V. A. Golubev, R. V. Miklyush, and Z. G. Rozantsev, Izv. Akad Nauk SSSR, Ser. Khim., 1972, 656 (Chem. Abstr., 1972, 77, 101344k).
5. (a) V. A. Golubev, R. V. Miklyush, and Z. G. Rozantsev, Izv. Akad Nauk SSSR, Ser. Khim., 1972, 656 (Chem. Abstr., 1972, 77, 101344k).
6. (b) V. A. Golubev and R. V. Miklyush, Zh. Org. Khim., 1972, 8, 1356 (Chem. Abstr., 1972, 77, 151087z).
7. (b) V. A. Golubev and R. V. Miklyush, Zh. Org. Khim., 1972, 8, 1356 (Chem. Abstr., 1972, 77, 151087z).
8. D. H. Hunter, Tetrahedron Lett., 1984, 25, 603.
9. M. F. Semmelhack and C. R. Schmid, J. Am. Chem. Soc., 1983, 105, 6732.
10. J. M. Bobbitt, M. C. F. Guttermuth, Z. Ma, and H. Tang, Heterocycles, 1990, 30, 1131; J. M. Bobbitt and M. C. Flores, Stud. Org. Chem., 1987, 30, 25.
11. J. M. Bobbitt, M. C. F. Guttermuth, Z. Ma, and H. Tang, Heterocycles, 1990, 30, 1131; J. M. Bobbitt and M. C. Flores, Stud. Org. Chem., 1987, 30, 25.
12. D. H. Hunter, J. S. Rocok, A. W. Ray, and Y. Z. Ponce, J. Org. Chem., 1988, 53, 1278.
13. T. Osa, Y. Kashiwagi, K. Mukai, A. Ohsawa, and J. M. Bobbitt, Chem. Lett., 1990, 75; Y. Kashiwagi, A. Ohsawa, T. Osa, Z. Ma, and J. M. Bobbitt, Chem. Lett., 1991, 581; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 81; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 257.
14. T. Osa, Y. Kashiwagi, K. Mukai, A. Ohsawa, and J. M. Bobbitt, Chem. Lett., 1990, 75; Y. Kashiwagi, A. Ohsawa, T. Osa, Z. Ma, and J. M. Bobbitt, Chem. Lett., 1991, 581; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 81; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 257.
15. T. Osa, Y. Kashiwagi, K. Mukai, A. Ohsawa, and J. M. Bobbitt, Chem. Lett., 1990, 75; Y. Kashiwagi, A. Ohsawa, T. Osa, Z. Ma, and J. M. Bobbitt, Chem. Lett., 1991, 581; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 81; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 257.
16. T. Osa, Y. Kashiwagi, K. Mukai, A. Ohsawa, and J. M. Bobbitt, Chem. Lett., 1990, 75; Y. Kashiwagi, A. Ohsawa, T. Osa, Z. Ma, and J. M. Bobbitt, Chem. Lett., 1991, 581; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 81; Y. Kashiwagi, H. Ono, and T. Osa, Chem. Lett., 1993, 257.
17. A. Deronzier, D. Limosin, and J. -C. Moutet, Electrochimica Acta, 1987, 32, 1643.
18. (±)-trans,cis-4-hydroxy-2,2,8a-trimethyldecahydroquinolinyl-N-oxyl was prepared according to the reported procedure: J. S. Roberts and C. Thomson, J. Chem. Soc., Perkin Trans. 2, 1972, 2129. Compound (1) was obtained by a conventional reaction of (±)-trans,cis-4-hydroxy-2,2,8a-trimethyldecahydroquinolinyl-N-oxyl with benzoyl chloride and was used in an isolated form. The electrocatalytic activity of this compound has not been reported.
19. 4 in acetonitrile). Cyclic potential sweeps were generated by a Hokuto Denko Model HABF-501 potentiostat/galvanostat. Cyclic voltammograms were recorded on a Graphtec Model WX1200 X-Y recorder. All electrochemical measurements were carried out at room temperature (ca. 20 °C).
20. J. M. Bobbitt and M. C. L. Flores, Heterocycles, 1988, 27, 509.
21. A. J. Bard and L. R. Faulkner, 'ELECTROCHEMICAL METHODS', John Wiley & Sons, Inc, New York, 1980, p. 215.
22. -1 flow rate, and detected by UV absorption at 254 nm.
23. Y. Yanagisawa, Y. Kashiwagi, F. Kurashima, J. Anzai, and T. Osa, Chem. Commun., 1996, 2745.