Abstract
1-Butyl-3-methylimidazolium bromide ([bmim]Br) as an ionic liquid promoted selectively the oxidation of alkyl arenes and alcohols to the corresponding carbonyl compounds with NaBrO3 in excellent yields under neutral conditions at the 70°C. Among the various ionic liquids examined, the [bmim]Br exhibited the best performances with NaBrO3. The ionic liquid can be recycled and reused for several runs without any significant loss of activity.
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CN Satterfield (2004) NoChapterTitle JE Backvall (Eds) Modern Oxidation Methods Wiley-VCH Germany
RC Larock (1999) Comprehensive Organic Transformations VCH New York 1234
RA Sheldon JK Kochi (1981) Metal-catalyzed Oxidation of Organic Compounds Academic New York 350
BM Trost I Fleming SV Ley (1991) Comprehensive Organic Synthesis NumberInSeries7 Pergamon Oxford
BZ Zhan A Thompson (2004) Tetrahedron 60 2917 Occurrence Handle10.1016/j.tet.2004.01.043 Occurrence Handle1:CAS:528:DC%2BD2cXhvV2ksrk%3D
Y Ishii S Sakaguchi T Iwahama (2001) Adv Synth Cat 343 393 Occurrence Handle10.1002/1615-4169(200107)343:5<393::AID-ADSC393>3.0.CO;2-K Occurrence Handle1:CAS:528:DC%2BD3MXmtVWltrs%3D
MJ Schultz MS Sigman (2006) Tetrahedron 62 8227 Occurrence Handle10.1016/j.tet.2006.06.065 Occurrence Handle1:CAS:528:DC%2BD28Xnt1Glt7Y%3D
K Weissermel HJ Arpe (1997) NoChapterTitle CR Lindley (Eds) Industrial Organic Chemistry EditionNumber3 VCH New York
D Kikuchi S Sakaguchi Y Ishii (1998) J Org Chem 63 6023 Occurrence Handle10.1021/jo972263q Occurrence Handle1:CAS:528:DyaK1cXkvF2gtbg%3D
M Biernstiel PJ Dhondt M Schalaf (2005) Tetrahedron 61 4911 Occurrence Handle10.1016/j.tet.2005.03.056
Takes K, Masuda O, Kaf O, Nishiyama Y, Sakguchi S, Ishii Y (1995) Chem Lett:871
S Sakguchi D Kikuchi Y Ishii (1997) Bull Chem Soc Jpn 70 2561 Occurrence Handle10.1246/bcsj.70.2561
S Kajigaeshi T Nakagawa N Nakasaki H Yamasaki S Fujisaki (1986) Bull Chem Soc Jpn 59 747 Occurrence Handle10.1246/bcsj.59.747 Occurrence Handle1:CAS:528:DyaL2sXhslGrug%3D%3D
Ho TL (1978) Synthesis: 936
H Tomioka K Oshima H Nozaki (1982) Tetrahedron Lett 23 539 Occurrence Handle10.1016/S0040-4039(00)86883-5 Occurrence Handle1:CAS:528:DyaL38XksFCrtbo%3D
Y Wang Y Zhao X Wang Z Duan (2002) Synth Commun 32 1781 Occurrence Handle10.1081/SCC-120004055 Occurrence Handle1:CAS:528:DC%2BD38Xlt1WmsLg%3D
G Hoist (1940) Kgl Fysiogrof Sallskap Lund 10 63
G Hoist (1941) Chem Abst 35 7808
L Metsger S Bittner (2000) Tetrahedron 56 1905 Occurrence Handle10.1016/S0040-4020(00)00098-3 Occurrence Handle1:CAS:528:DC%2BD3cXitlahs70%3D
A Shaabani A Bazgir MB Teimouri (2002) Synth Commun 32 675 Occurrence Handle10.1081/SCC-120002504 Occurrence Handle1:CAS:528:DC%2BD38Xit1Kntrs%3D
AC Chatterji SKZ Roy (1972) Phys Chem 250 137 Occurrence Handle1:CAS:528:DyaE38Xltl2hsr8%3D
AC Chatterji SKZ Roy (1972) Chem Abstr 77 39201z
A Shaabani A Bazgir K Soleimani P Salehi (2003) Synth Commun 33 2935 Occurrence Handle10.1081/SCC-120022465 Occurrence Handle1:CAS:528:DC%2BD3sXmvFCns78%3D
A Shaabani K Soleimani A Bazgir (2004) Synth Commun 34 3303 Occurrence Handle10.1081/SCC-200030562 Occurrence Handle1:CAS:528:DC%2BD2cXnsVaju7k%3D
A Shaabani DG Lee (2003) Sulfur Lett 26 43 Occurrence Handle10.1080/0278611021000048703 Occurrence Handle1:CAS:528:DC%2BD3sXlt1Crtrk%3D
Shaabani A, Ameri M (1998) J Chem Research (S): 100
A Shaabani MB Teimouri HR Safaei (2000) Synth Commun 30 265 Occurrence Handle10.1080/00397910008087317 Occurrence Handle1:CAS:528:DC%2BD3cXhtFKhsro%3D
A Shaabani AR Karimi (2001) Synth Commun 31 759 Occurrence Handle10.1081/SCC-100103266 Occurrence Handle1:CAS:528:DC%2BD3MXksFGhtLs%3D
D Kikuchi S Sakaguchi Y Ishii (1998) J Org Chem 63 6023 Occurrence Handle10.1021/jo972263q Occurrence Handle1:CAS:528:DyaK1cXkvF2gtbg%3D
MJ Earle KR Seddon (2000) Pure Appl Chem 72 1391 Occurrence Handle10.1351/pac200072071391 Occurrence Handle1:CAS:528:DC%2BD3cXotFKqsLs%3D
T Welton (1999) Chem Rev 99 2071 Occurrence Handle10.1021/cr980032t Occurrence Handle1:CAS:528:DyaK1MXkt1artrw%3D
P Wasserscheid W Keim (2000) Angew Chem Int Ed 39 3773 Occurrence Handle10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
J Dupont RF de Souza PAZ Suarez (2002) Chem Rev 102 3667 Occurrence Handle10.1021/cr010338r Occurrence Handle1:CAS:528:DC%2BD38Xmt1Oqur4%3D
Sheldon R (2001) Chem Commun:2399
P Wasserscheid T Welton (2002) Ionic Liquids in Synthesis Wiley-VCH Weinheim
CM Gordon (2001) Appl Catal A Chem 222 101 Occurrence Handle10.1016/S0926-860X(01)00834-1 Occurrence Handle1:CAS:528:DC%2BD38XjvFSm
J Muzart (2006) Adv Synth Cat 348 275 Occurrence Handle10.1002/adsc.200505273 Occurrence Handle1:CAS:528:DC%2BD28XitFeqt7Y%3D
A Shaabani A Bazgir M Abdoli (2002) Synth Commun 32 683 Occurrence Handle10.1081/SCC-120002504
A Shaabani HR Safaei A Bazgir (2000) Iran J Chem Chem Eng 19 47 Occurrence Handle1:CAS:528:DC%2BD3MXislyksLs%3D
A Shaabani A Bazgir F Teimouri DG Lee (2002) Tetrahedron Lett 43 5165 Occurrence Handle10.1016/S0040-4039(02)00976-0 Occurrence Handle1:CAS:528:DC%2BD38XkvVenurw%3D
A Shaabani DG Lee (2001) Tetrahedron Lett 42 5833 Occurrence Handle10.1016/S0040-4039(01)01129-7 Occurrence Handle1:CAS:528:DC%2BD3MXlsFOlur0%3D
A Shaabani P Mirzaei S Naderi DG Lee (2004) Tetrahedron 60 11415 Occurrence Handle10.1016/j.tet.2004.09.087 Occurrence Handle1:CAS:528:DC%2BD2cXpsVKmtb4%3D
Laboratory Chemicals and Analytical Reagents, Fluka Comp 1999–2000
Chemicals Reagents, Merck Comp 2005–2007
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Correspondence: Ahmad Shaabani, Department of Chemistry, Shahid Beheshti University, P.O. Box 19839-4716, Tehran, Iran.
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Shaabani, A., Farhangi, E. & Rahmati, A. Ionic liquid promoted selective oxidation of organic compounds with NaBrO3 . Monatsh Chem 139, 905–908 (2008). https://doi.org/10.1007/s00706-007-0840-x
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DOI: https://doi.org/10.1007/s00706-007-0840-x