Selective oxidation of 1,2-diols by electrochemical method using organotin compound and bromide ion as mediators

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 651-654

  Maki, Toshihide ^a   Fukae, Kazuhiro ^a   Harasawa, Hitomi ^a   Ohishi, Takahiro ^a   Matsumura, Yoshihiro ^a   Onomura, Osamu ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BROMIDE; ORGANOTIN COMPOUND;

ARTICLE; ELECTROCHEMISTRY; ELECTROLYSIS; OXIDATION; TECHNIQUE;

EID: 0032509937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10709-2     Document Type: Article

References (13)

1. 1. a) David, S. C.R.Acad.Sci.Paris, Serie C 1974, 278, 1051-1053.
2. b) David, S.; Theffry, A.J. Chem Soc. Perkin I 1979, 1568-1573.
3. 2. Hanessian, S.; Roy, R. J.Am.Chem.Soc. 1979, 101, 5839-5841.
4. 3. a) Tsuda,Y.; Hanajima, M.; Yoshimoto, K.Chem. Pharm. Bull. 1983, 31, 3778-3788.
5. b) Tsuda, Y.; Hanajima, M.; Matsuhira, N.; Okuno, Y.; Kanemitsu, K. Chem. Pharm. Bull. 1989, 37, 2344-2350.
6. c) Liu, H.M.; Sato, Y.; Tsuda, Y. Chem. Pharm. Bull. 1993, 41, 491-501.
7. 4. Fernandez-Mayoralas, A.; Bernabe, M.; Martin-Lomas, M. Tetrahedron 1988, 44, 4877-4882.
8. 5. Some other 1,2-diols were also oxidized under the similar reaction conditions to the corresponding keto alcohols (the isolated yields: 87% for 4-t-butyl-1,2-cyclohexanediol; 74% for 1,2-cycloheptanediol; 33% for 1,2-cyclopentanediol; 47% for meso-hydrobenzoin).
9. 6. Dibutyltin oxide was hardly dissolved in methanol at room temperature.
10. 7. Keto alcohol 5 was easily dimerized when isolated 5 was allowed to stand at room temperature. Thus, the yields shown in Table 1 were obtained by means of GLC immediately after the electrolysis.
11. +.
12. 9. Kashimura, S. J.Synth.Org.Chem.Jpn. 1985, 43, 549-556.
13. 10. In order to easily determine the ratio of recovered cis-4/trans-4, the reaction mixture was benzoylated by treatment with excess benzoyl chloride in the presence of dimethylaminopyridine in methylene chloride.