One-pot synthesis of phenol and cyclohexanone from cyclohexylbenzene catalyzed by N-hydroxyphthalimide (NHPI)

Tetrahedron

Volumn 61, Issue 22, 2005, Pages 5219-5222

  Aoki, Yasuhiro ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

Aerobic oxidation; Cyclohexanone; Hydroperoxide; N Hydroxyphthalimide; Phenol

Indexed keywords

4 HYDROXYACETOPHENONE; BENZENE DERIVATIVE; CYCLOHEXANONE; CYCLOHEXYLAMINE DERIVATIVE; N HYDROXYPHTHALIMIDE; PHTHALIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 18844405936     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.079     Document Type: Article

References (18)

1. J. Rigueras, P.W. Scullard, and A.R. Mack J. Org. Chem. 36 1971 3497
2. K. Haghbeen, and E.W. Tan J. Org. Chem. 63 1998 4503
3. A. Knop, and W. Scheib Chemistry and Application of Phenolic Resin 1979
4. H. Hock, and S. Lang Ber. Dtsch. Chem. Ges. B77 1944 257
5. W. Jordan, H. van Barneveld, O. Gerlich, M.K. Boymann, and J. Ullrich Ullmann's Encyclopedia of Industrial Organic Chemicals Vol. A9 1985 Wiley-VCH Weinheim pp 299-312
6. R.A. Sheldon, and J.K. Kochi Metal-catalyzed Oxidations of Organic Compounds 1981 Academic New York
7. I.W.C.E. Arends, M. Sasiidharan, A. Kuhnle, M. Duda, C. Jost, and R.A. Sheldon Tetrahedron 58 2002 9055
8. Several works on the formation of CHBPO from cyclohexylbenzene followed by transformation into phenol and cyclohexanone have been reported; (a) Van, B. H.; Pompetzki, W.; Gerlich, O.; Kleinloh, W. Eur. Patent 1,088,808; Chem. Abstr. 2001, 134, 266097. (b) Wun, Y. U.S. Patent 4,328,372; Chem. Abstr. 1982, 97, 55367. (c) Velenyi, L. J.; Uebele, C. E.; Dolhyj, S. R. U.S. Patent 4,299,991; Chem. Abstr.. 1982, 96, 51997. (d) Koshel, G. N.; Glazyrina, I. I.; Farberov, M. I.; Bychkov, B. N.; Kirichenko, G. N. U.S. Patent 586,157; Chem. Abstr. 1978, 88, 89364
9. Several works on the formation of CHBPO from cyclohexylbenzene followed by transformation into phenol and cyclohexanone have been reported; (a) Van, B. H.; Pompetzki, W.; Gerlich, O.; Kleinloh, W. Eur. Patent 1,088,808; Chem. Abstr. 2001, 134, 266097. (b) Wun, Y. U.S. Patent 4,328,372; Chem. Abstr. 1982, 97, 55367. (c) Velenyi, L. J.; Uebele, C. E.; Dolhyj, S. R. U.S. Patent 4,299,991; Chem. Abstr.. 1982, 96, 51997. (d) Koshel, G. N.; Glazyrina, I. I.; Farberov, M. I.; Bychkov, B. N.; Kirichenko, G. N. U.S. Patent 586,157; Chem. Abstr. 1978, 88, 89364
10. Several works on the formation of CHBPO from cyclohexylbenzene followed by transformation into phenol and cyclohexanone have been reported; (a) Van, B. H.; Pompetzki, W.; Gerlich, O.; Kleinloh, W. Eur. Patent 1,088,808; Chem. Abstr. 2001, 134, 266097. (b) Wun, Y. U.S. Patent 4,328,372; Chem. Abstr. 1982, 97, 55367. (c) Velenyi, L. J.; Uebele, C. E.; Dolhyj, S. R. U.S. Patent 4,299,991; Chem. Abstr.. 1982, 96, 51997. (d) Koshel, G. N.; Glazyrina, I. I.; Farberov, M. I.; Bychkov, B. N.; Kirichenko, G. N. U.S. Patent 586,157; Chem. Abstr. 1978, 88, 89364
11. Several works on the formation of CHBPO from cyclohexylbenzene followed by transformation into phenol and cyclohexanone have been reported; (a) Van, B. H.; Pompetzki, W.; Gerlich, O.; Kleinloh, W. Eur. Patent 1,088,808; Chem. Abstr. 2001, 134, 266097. (b) Wun, Y. U.S. Patent 4,328,372; Chem. Abstr. 1982, 97, 55367. (c) Velenyi, L. J.; Uebele, C. E.; Dolhyj, S. R. U.S. Patent 4,299,991; Chem. Abstr.. 1982, 96, 51997. (d) Koshel, G. N.; Glazyrina, I. I.; Farberov, M. I.; Bychkov, B. N.; Kirichenko, G. N. U.S. Patent 586,157; Chem. Abstr. 1978, 88, 89364
12. D.H. Hey, C.J.M. Stirling, and G.H. Williams J. Chem. Soc., Abstr. 1957 1054
13. Chem. Abstr. 51 1957 56568
14. O. Fukuda, S. Sakaguchi, and Y. Ishii Adv. Synth. Catal. 343 2001 809
15. T. Iwahama, G. Hatta, S. Sakaguchi, and Y. Ishii Chem. Commun. 2000 163
16. Y. Tashiro, T. Iwahama, S. Sakaguchi, and Y. Ishii Adv. Synth. Catal. 343 2001 220
17. In our previous works, we succeeded the recovery of NHPI catalysts in the nitration and nitrososation of cycloalkanes without use of transition metal salts as promoter; (a) S. Sakaguchi, Y. Nishiwaki, T. Kitamura, and Y. Ishii Angew. Chem., Int. Ed. 40 2001 222
18. T. Hirabayashi, S. Sakaguchi, and Y. Ishii Angew. Chem., Int. Ed. 43 2004 1120