Electrooxidation of alcohols in a disperse system with N-oxyl-immobilized polyethylene particles as disperse phase and aqueous NaHCO3/NaBr as disperse media: A totally closed electrolysis system

Synlett

Volumn , Issue 7, 2003, Pages 951-954

  Tanaka, Hideo ^a   Kubota, Jun ^a   Itogawa, Shin Ji ^a   Ido, Toru ^a   Kuroboshi, Manabu ^a   Shimamura, Kaoru ^a   Uchida, Tetsuya ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Alcohol; Aqueous disperse media; Disperse system; Electrooxidation; N oxyl; Polyethylene particles

Indexed keywords

ALCOHOL DERIVATIVE; BICARBONATE; CHLOROBENZENE; NITRIC ACID; POLYETHYLENE DERIVATIVE; SODIUM BROMIDE;

ALCOHOL OXIDATION; AQUEOUS SOLUTION; ARTICLE; BROMINATION; CHEMICAL MODIFICATION; DISPERSION; ELECTROLYSIS; FILTRATION; HEATING; PARTICULATE MATTER; RECYCLING;

EID: 0038576724     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. (a) Semmelhack, M. F.; Chou, C. S.; Cortes, D. A. J. Am. Chem. Soc. 1983, 105, 4492.
2. (b) Ma, Z.; Huang, Q.; Bobbitt, J. M. J. Org. Chem. 1993, 58, 4837.
3. (c) Yanagisawa, Y.; Kashiwagi, Y.; Kurashima, F.; Anzai, J.; Osa, T.; Bobbitt, J. M. Chem. Lett. 1996, 1043.
4. (d) Kashiwagi, Y.; Yanagisawa, Y.; Kurashima, F.; Anzai, J.; Osa, T.; Bobbitt, J. M. J. Chem. Soc., Chem. Commun. 1996, 27, 45.
5. (e) Kashiwagi, Y.; Kurashima, F.; Kikuchi, C.; Anzai, J.; Osa, T.; Bobbitt, J. M. Tetrahedron Lett. 1999, 40, 6469; and references cited therein.
6. 2O two phase system for N-oxyl-mediated electrooxidation of alcohols: (a) Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462. (b) Torii, S.; Inokuchi, T.; Matsumoto, S.; Saeki, T.; Oki, T. Bull. Chem. Soc. Jpn. 1990, 63, 852. (c) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416. (d) Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411. (e) Kuroboshi, M.; Yoshihisa, H.; Cortona, M. N.; Kawakami, Y.; Gao, Z.; Tanaka, H. Tetrahedron Lett. 2000, 41, 8131. (f) Electrooxidation of carbohydrate in aqueous solution: Schnatbaum, K.; Schafer, H. J. Synthesis 1999, 864.
7. 2O two phase system for N-oxyl-mediated electrooxidation of alcohols: (a) Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462. (b) Torii, S.; Inokuchi, T.; Matsumoto, S.; Saeki, T.; Oki, T. Bull. Chem. Soc. Jpn. 1990, 63, 852. (c) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416. (d) Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411. (e) Kuroboshi, M.; Yoshihisa, H.; Cortona, M. N.; Kawakami, Y.; Gao, Z.; Tanaka, H. Tetrahedron Lett. 2000, 41, 8131. (f) Electrooxidation of carbohydrate in aqueous solution: Schnatbaum, K.; Schafer, H. J. Synthesis 1999, 864.
8. 2O two phase system for N-oxyl-mediated electrooxidation of alcohols: (a) Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462. (b) Torii, S.; Inokuchi, T.; Matsumoto, S.; Saeki, T.; Oki, T. Bull. Chem. Soc. Jpn. 1990, 63, 852. (c) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416. (d) Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411. (e) Kuroboshi, M.; Yoshihisa, H.; Cortona, M. N.; Kawakami, Y.; Gao, Z.; Tanaka, H. Tetrahedron Lett. 2000, 41, 8131. (f) Electrooxidation of carbohydrate in aqueous solution: Schnatbaum, K.; Schafer, H. J. Synthesis 1999, 864.
9. 2O two phase system for N-oxyl-mediated electrooxidation of alcohols: (a) Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462. (b) Torii, S.; Inokuchi, T.; Matsumoto, S.; Saeki, T.; Oki, T. Bull. Chem. Soc. Jpn. 1990, 63, 852. (c) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416. (d) Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411. (e) Kuroboshi, M.; Yoshihisa, H.; Cortona, M. N.; Kawakami, Y.; Gao, Z.; Tanaka, H. Tetrahedron Lett. 2000, 41, 8131. (f) Electrooxidation of carbohydrate in aqueous solution: Schnatbaum, K.; Schafer, H. J. Synthesis 1999, 864.
10. 2O two phase system for N-oxyl-mediated electrooxidation of alcohols: (a) Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462. (b) Torii, S.; Inokuchi, T.; Matsumoto, S.; Saeki, T.; Oki, T. Bull. Chem. Soc. Jpn. 1990, 63, 852. (c) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416. (d) Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411. (e) Kuroboshi, M.; Yoshihisa, H.; Cortona, M. N.; Kawakami, Y.; Gao, Z.; Tanaka, H. Tetrahedron Lett. 2000, 41, 8131. (f) Electrooxidation of carbohydrate in aqueous solution: Schnatbaum, K.; Schafer, H. J. Synthesis 1999, 864.
11. 2O two phase system for N-oxyl-mediated electrooxidation of alcohols: (a) Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J. Org. Chem. 1990, 55, 462. (b) Torii, S.; Inokuchi, T.; Matsumoto, S.; Saeki, T.; Oki, T. Bull. Chem. Soc. Jpn. 1990, 63, 852. (c) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416. (d) Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411. (e) Kuroboshi, M.; Yoshihisa, H.; Cortona, M. N.; Kawakami, Y.; Gao, Z.; Tanaka, H. Tetrahedron Lett. 2000, 41, 8131. (f) Electrooxidation of carbohydrate in aqueous solution: Schnatbaum, K.; Schafer, H. J. Synthesis 1999, 864.
12. Tanaka, H.; Kawakami, Y.; Goto, K.; Kuroboshi, M. Tetrahedron Lett. 2001, 42, 445.
13. Recently, transition metal/TEMPO-catalyzed aerobic oxidation has been reported as an environmentally benign procedure for oxidation of alcohols. See for example: Sheldon, R. A.; Arends, I. W. C. E.; Brink, G.-J. T.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774.
14. (a) Killer, A.; Udagawa, Y. J. Polym. Sci. 1970, 8, 19.
15. (b) Shimamura, K.; Munesawa, Y.; Uchida, T.; Hikasa, N. Polym. Adv. Tech. 2002, 13, 205.
16. -1 due to carboxylic acid, which disappeared during the subsequent treatment with 4-amino-2,2,6,6-tetramethylpiperidine-N-oxyl.
17. Carried out on a Yanaco GC 6800 with a Quadrex Corporation fused silica glass capillary column (methyl phenyl 5:25 m x 0.25 mm i.d.). Column 100°C, injector 270°C, detector 300°C, carrier gas, He; flow rate, 26 mL/min.
18. -, would not act as the oxidant for generation of N-oxoammonium ion from N-oxyl.