Catalytic oxidation of various alcohols to the corresponding carbonyl compounds with N-chlorosuccinimide using a catalytic amount of sulfenamide

Chemistry Letters

Volumn , Issue 8, 2001, Pages 846-847

  Mukaiyama, Teruaki ^a   Matsuo, Jun Ichi ^a   Iida, Daisuke ^a   Kitagawa, Hideo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035538901     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.846     Document Type: Article

References (10)

1. TPAP: tetrapropylammonium perruthenate. W. P. Griffith, S. V. Ley, G. P. Whitcombe, and A. D. White, J. Chem. Soc., Chem. Commun., 1987, 1625.
2. A. J. Mancuso and D. Swern, Synthesis, 1981, 165.
3. a) T. Mukaiyama, J. Matsuo, and M. Yanagisawa, Chem. Lett., 2000, 1072.
4. b) J. Matsuo, H. Kitagawa, D. Iida, and T. Mukaiyama, Chem. Lett., 2001, 150.
5. a) E. J. Corey and C. U. Kim, J. Am. Chem. Soc., 94, 7586 (1972).
6. b) T. Mukaiyama, M. Tsunoda, and K. Saigo, Chem. Lett., 1975, 691.
7. 5b and tert-butylamine. See: a) Y. Miura, H. Asada, and M. Kinoshita, Bull. Chem. Soc. Jpn., 50, 1855 (1977).
8. b) A. G. M. Barrett, D. Dhanak, G. G. Graboski, and S. J. Taylor, Org. Synth., 68, 8 (1990).
9. In the case of N,N-dialkylsulfenamides, alkylamino-succinimidosulfonium chlorides were obtained on treatment with NCS. See: M. Haake and H. Benack, Synthesis, 1976, 308.
10. Powdered potassium carbonate was dried in vacuo by heating it with a heat-gun. Molecular sieves and Drierite® were also dried in vacuo at 250 °C for 12 h.