Efficient oxidation of cycloalkanols by sodium nitrite with molecular oxygen in trifluoroacetic acid

Tetrahedron Letters

Volumn 45, Issue 44, 2004, Pages 8221-8224

  Matsumura, Yoshihiro ^a   Yamamoto, Yutaka ^a   Moriyama, Noriaki ^a   Furukubo, Shigeru ^a   Iwasaki, Fumiaki ^b   Onomura, Osamu ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b TOKUYAMA CORPORATION   (Japan)

Author keywords

Adipic acid; Cyclohexanol; Nitrosonium ion; Oxidation; Trifluoroacetic acid

Indexed keywords

ALKANOL; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANOL; OXYGEN; SODIUM NITRITE; TRIFLUOROACETIC ACID;

ARTICLE; ATMOSPHERE; MEDICAL RESEARCH; OXIDATION; QUANTITATIVE ANALYSIS;

EID: 4744348829     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.037     Document Type: Article

References (28)

1. J.R.L. Smith, and R.N. Loeppky J. Am. Chem. Soc. 89 1967 1147 1157
2. G.A. Olah, and T.-L. Ho Synthesis 1976 609 610
3. G.A. Olah, and T.-L. Ho Synthesis 1976 610 611
4. T.-L. Ho, and G.A. Olah J. Org. Chem. 42 1977 3097 3098
5. G.A. Olah, J.G. Shih, and B.P. Singh J. Org. Chem. 48 1983 3356 3358
6. M. Rogić, J. Vitrone, and M.D. Swerdloff J. Am. Chem. Soc. 97 1975 3848 3850
7. C.-Y. Shiue, and L.D. Clapp J. Org. Chem. 36 1971 1169 1170
8. M. Rogić, J. Vitrone, and M.D. Swerdloff J. Am. Chem. Soc. 99 1977 1156 1171
9. B.S. Tovrog, S.E. Diamond, F. Mares, and A. Szalkiewicz J. Am. Chem. Soc. 103 1981 3522 3526
10. S.A. Nyarady, and R.E. Sievers J. Am. Chem. Soc. 107 1985 3726 3727
11. T. Nishiguchi, and F. Asano J. Org. Chem. 54 1989 1531 1535
12. A. Cornelis, and P. Laszlo Synthesis 1985 909 918
13. B.P. Bandgar, V.S. Sadavarte, and L.S. Uppalla J. Chem. Soc., Perkin Trans. 1 2000 3559 3560
14. 2 in an aqueous trifluoroacetic acid afforded the corresponding carbonyl compounds but it has pointed out that the oxidation products carbonyl compounds are not further oxidized by the use of excess sodium nitrite: M.A. Rodkin, M.M. Shpern, A.V. Cheprakov, D.I. Makhon'kov, R.E. Mardaleishvili, and I.P. Beletskaya Zh. Org. Khim. 24 1988 488 495
15. A. Castellan, J.C.J. Bart, and S. Cavallaro Catal. Today 9 1991 255 283
16. From cyclohexane: Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama, and Y. Nishiyama J. Org. Chem. 61 1996 4520 4526
17. From cyclohexene: K. Sato, M. Aoki, and R. Noyori Science 281 1998 1646 1647
18. Y. Usui, and K. Sato Green Chem. 5 2003 373 375
19. L.F. Fieser, and M. Fieser Reagents for Organic Synthesis 1967 John Wiley and Sons New York p 733
20. B. Ellis Org. Syn., Coll. 1 1932 18 20
21. J.R.L. Smith, D.I. Richards, C.B. Thomas, and M. Whittaker J. Chem. Soc., Perkin Trans. 2 1985 1677 1685
22. E.J. Strojny, R.T. Iwamasa, and L.K. Frevel J. Am. Chem. Soc. 93 1971 1171 1178
23. J.R.L. Smith, D.I. Richartds, C.B. Thomas, and M. Whittaker J. Chem. Soc., Perkin Trans. 2 1992 605 611
24. J.R.L. Smith, C.B. Thomas, and M. Whittaker J. Chem. Soc., Perkin Trans. 2 1993 2191 2194
25. F. Minisci, F. Recupero, C. Gambarotti, C. Punta, and R. Paganelli Tetrahedron Lett. 44 2003 6919 6922
26. P. Strazzolini, and A. Runcio Eur. J. Org. Chem. 2003 526 536
27. A possibility of adducts of trifluoroacetic acid to A cannot be excluded as intermediates instead of B-D
28. The used trifluoroacetic acid was recovered by the reported procedure: U.A. Spitzer, and R. Stewart J. Org. Chem. 39 1974 3936 3937