Unique salt effect on the high yield synthesis of acid-labile terpene oxides using hydrogen peroxide under acidic aqueous conditions

Synlett

Volumn , Issue 19, 2011, Pages 2819-2822

  Hachiya, Houjin ^a   Kon, Yoshihiro ^a   Ono, Yutaka ^a   Takumi, Kiyoshi ^b   Sasagawa, Naoki ^b   Ezaki, Yoichiro ^b   Sato, Kazuhiko ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b Arakawa Chemical Industries   (Japan)

Author keywords

catalysis; epoxides; green chemistry; oxidation; terpenoids

Indexed keywords

HYDROGEN PEROXIDE; TERPENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENVIRONMENTAL TEMPERATURE; EPOXIDATION; HYDROLYSIS; REACTION TIME; SOLUBILITY; SYNTHESIS;

EID: 81855198892     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289860     Document Type: Article

References (37)

1. Ullmanns Encyclopedia of Industrial Chemistry 5th ed., Vol. A9 Gerhartz W Yamamoto Y S. Kaudy L Rounsaville J F. Schulz G Wiley-VCH Weinheim 1987 531
2. Kirk-Othmer Encyclopedia of Chemical Technology 4th ed., Vol. 9 Kroschwitz J I. Howe-Grant M Wiley New York 1994 377
3. Kirk-Othmer Encyclopedia of Chemical Technology 4th ed., Vol. 9 Kroschwitz J I. Howe-Grant M Wiley New York 1994 730
4. Larock R C., In Comprehensive Organic Transformations 2nd ed. Wiley New York 1999 915
5. Strukul G, In Catalytic Oxidations with Hydrogen Peroxide as Oxidant Kluwer Academic Publishers Dordrecht 1992
6. Jones C W., In Applications of Hydrogen Peroxide and Derivatives RSC Cambridge 1999
7. Trost B M., Science 1991 254 1471
8. Sheldon R A., Chem. Ind. 1992 903
9. For recent reviews, see: Applied Homogeneous Catalysis with Organometallic Compounds 2nd ed. Cornils B Herrmann W A. Wiley-VCH Weinheim 2002
10. Lane B S., Burgess K, Chem. Rev. 2003 103 2457
11. Grigoropoulou G, Clark J H., Elings J A., Green Chem. 2003 5 1
12. Modern Oxidation Methods Bäckvall J.-E Wiley-VCH Weinheim 2004
13. Mizuno N, Yamaguchi K, Kamata K, Coord. Chem. Rev. 2005 249 1944
14. Payne G B., Williams P H., J. Org. Chem. 1959 24 54
15. Venturello C, Alneri E, Ricci M, J. Org. Chem. 1983 48 3831
16. Ishii Y, Yamawaki K, Ura T, Yamada H, Yoshida T, Ogawa M, J. Org. Chem. 1988 53 3587
17. Sato K, Aoki M, Ogawa M, Hashimoto T, Noyori R, J. Org. Chem. 1996 61 8310
18. Sato K, Aoki M, Ogawa M, Hashimoto T, Panyella D, Noyori R, Bull. Chem. Soc. Jpn. 1997 70 905
19. Noyori R, Aoki M, Sato K, Chem. Commun. 2003 1977
20. Sienel G, Rieth R, In Ullmanns Encyclopedia of Industrial Chemistry 6th ed., Vol. 12 Wiley-VCH Weinheim 2003 279
21. Eggersdorfer M, In Ullmanns Encyclopedia of Industrial Chemistry 6th ed., Vol. 35 Wiley-VCH Weinheim 2003 653
22. Swift K A. D., Top. Catal. 2004 27 143
23. Corma A, Iborra S, Velty A, Chem. Rev. 2007 107 2411
24. Bicas J L., Dionísio A P., Pastore G M., Chem. Rev. 2009 109 4518
25. Kon Y, Ono Y, Matsumoto T, Sato K, Synlett 2009 1095
26. Kon Y, Hachiya H, Ono Y, Matsumoto T, Sato K, Synthesis 2011 1092
27. Hou S.-Y, Zhou Z.-H, Lin T.-R, Wan H.-L, Eur. J. Inorg. Chem. 2006 1670
28. Maheswari P U., Tang X, Hage R, Gamez P, Reedijk J, J. Mol. Catal. A: Chem. 2006 258 295
29. Kolehmainen E, Laihia K, Heinänen M, Rissanen K, Fröhlich R, Korvola J, Mänttäri P, Kauppinen R, J. Chem. Soc., Perkin Trans. 2 1993 641
30. Kopperman H L., Hallcher R C. Sr, Riehl A, Carlson R M., Caple R, Tetrahedron 1976 32 1621
31. Liu W, Rosazza J P. N., Synth. Commun. 1996 26 2731
32. Grigoropoulou G, Clark J H., Tetrahedron Lett. 2006 47 4461
33. McDevit W F., Long F A., J. Am. Chem. Soc. 1952 74 1773
34. Long F A., McDevit W F., Chem. Rev. 1952 51 119
35. Hofmeister F, Arch. Exp. Pathol. Pharmacol. 1887 24 247
36. Poulson S R., Harrington R R., Drever J I., Talanta 1999 48 633
37. Görgényi M, Dewulf J, Langenhove H V., Héberger K, Chemosphere 2006 65 802