Abstract
Two kinds of task-specific ionic liquids (Ils) composed of imidazolinium or pyridinium cations with a carboxy group and hydrogensulfate as counterion have been synthesised and their application in oxidation of olefins has been studied. The carbonyl compounds were obtained from the oxidation of chain olefins, and 1,2-cycloalkandiols were obtained from cycloalkenes in the novel oxidation systems which are easily manipulated. The products can be easily isolated from the reaction system and the ILs can readily be recovered and reused.
References
1.
Welton T.
, Chem. Rev. , 1999 , 99 , 2071 .
2.
Wasserscheid P.
, and
Keim W.
, Angew. Chem., Int. Ed. Eng. , 2000 , 39 , 3772 .
3.Aqueous-Phase Organometallic Catalysts: Concepts and Applications , Wiley-VCH : Weinheim , B. Cornils and W.A. Herrmann, Ed. 1998 .
4.
Visser A.E.
,
Swatlowski R. P.
, and
Rogers R. D.
, Green Chem. , 2000 , 2 , 1 .
5.
Armstrong D.W.
,
He L.
, and
Lin S. Y.
, Anal. Chem. , 1999 , 71 , 3873 .
6.
Freemantal M.
, Chem. Eng. News , 2000 , 15 , 37 .
7.Ionic Liquids in Synthesis , Wiley-VCH Verlag GmbH & Co. KGaA , P. Wasserscheid and T, Welton, Ed.; 2002 , p. 33 .
8.
Visser A.E.
,
Holbrey J. D.
, and
Rogers R. D.
, Chem. Commun. , 2001 , 2484 .
9.
Visser A.E.
,
Swatloski R. P.
,
Reichert W. M.
,
Mayton R.
,
Sheff S.
,
Wierzbichi A.
,
Davis J. H.
Jr.
, and
Rogers R. D.
, Chem. Commun. , 2001 , 135 .
10.
Merrigan T.L.
,
Bates E. D.
,
Dorman S. C.
, and
Davis J. H.
Jr.
, Chem. Commun. , 2000 , 2051 .
11.
Davis J.H.
Jr.
,
Forrester K. J.
, and
Merrigan T.
, Tetrahedron Lett. , 1998 , 39 , 8955 .
12.
(a)
Dubreuil J.F.
, and
Bazureau J. P.
, Tetrahedron Lett. , 2000 , 41 , 7351 .
13.
Dubreuil J.F.
, and
Bazureau J. P.
, Tetrahedron Lett. , 2001 , 42 , 6097 .
14.
Dubreuil J.F.
,
Famlart M. H.
, and
Bazureau J. P.
, Org. Process Res. Dev. , 2002 , 6 , 374 .
15.
Dubreuil J.F.
, and
Bazureau J. P.
, Tetrahedron , 2003 , 59 , 6121 .
16.
Anjaiah S.
,
Chandrasekhar S.
, and
Grée R.
, Tetrahedron Lett. , 2004 , 45 , 569 .
17.
(a)
Gu Y.
,
Shi F.
, and
Deng Y.
, Catal. Commun. , 2003 , 4 , 597 .
18.
Li D.
,
Shi F.
,
Guo S.
, and
Deng Y.
, Tetrahedron Lett. , 2004 , 45 , 265 .
19.
Miao W.
, and
Chan T. H.
, Org. Lett. , 2003 , 5 , 5003 .
20.
Bates E.D.
,
Mayton R. D.
,
Ntai I.
, and
Davis J. H.
Jr.
, J. Am. Chem. Soc. , 2002 , 124 , 926 .
21.
Wasserscheid P.
,
Bösmann A.
, and
Bolm C.
, Chem. Commun. , 2002 , 200 .
22.
Bao W.
,
Wang Z.
, and
Li Y.
, J. Org. Chem. , 2003 , 68 , 591 .
23.
Handy S.T.
,
Okello M.
, and
Dickenson G.
, Org. Lett. , 2003 , 5 , 2513 .
24.
Wasserscheid P.
,
Sesing M.
, and
Korth W.
, Green Chem. , 2002 , 4 , 134 .
25.Advanced Organic Chemistry , McGraw-Hill Book Co. : New York , M.B. Smith and J. March, 5th ed. 2000 , pp. 1542 .
26.Dictionary of Organic Compounds , Mac Dictionary of Organic Compounds , Mack Printing Com. , Easton , Pennsylvaia, J. Buckingham, 5th ed., 1982 .
27.Nuclear Magnetic Resonance Spectra , Sadlter Research laboratories, Inc. Rearchers , Editors and Publishers, 1980 .
28.
Seaman J.I.
, and
Zifler H.
, Tetrahedron , 1968 , 24 , 965 .
29.
Tagaki W.
, and
Mitsui T.
, J. Org. Chem. , 1960 , 25 , 1476 .
30.
Barak G.
, and
Sasson Y.
, Chem. Commun. , 1987 , 1266 .
31.
Namboodiri V.V.
,
Varma R. S.
,
Demessie E. S.
, and
Pillai U. R.
, Green Chem. , 2002 , 4 , 170 .
32.
Antonelli E.
,
D'Aloisio R.
,
Gambaro M.
,
Fiorani T.
, and
Venturello C.
, J. Org. Chem. , 1998 , 63 , 7190 .
