Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(4): 583-586
DOI: 10.1055/s-0028-1083317
DOI: 10.1055/s-0028-1083317
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Methylated Imidazolinium-Dithiocarboxylates: Two Representatives of a New Class of Ionic Liquids
Further Information
Received
7 August 2008
Publication Date:
09 January 2009 (online)
Publication History
Publication Date:
09 January 2009 (online)
Abstract
The work describes the methylation of chiral and achiral imidazolinium-dithiocarboxylates. The resulting salts qualify as a novel class of ionic liquids after an anion metathesis was performed. Their NMR and UV/Vis spectra were studied.
Key words
ionic liquids - chirality - chiral cations - imidazolinium salts - zwitterions
-
1a
Wasserscheid P.Welton T. Ionic Liquids in Synthesis Wiley-VCH; Weinheim: 2002. p.Vol. 1 -
1b
Wasserscheid P.Welton T. Ionic Liquids in Synthesis 2nd ed., Vol. 2: Wiley-VCH; Weinheim: 2008. - 2
Rogers RD.Seddon KR. Ionic Liquids as Green Solvents: Progress and Prospects American Chemical Society; Washington DC: 2003. p.2-12 -
3a
Chowdhury S.Mohan RS.Scott JL. Tetrahedron 2007, 63: 2363 -
3b
Jurčík V.Wilhelm R. Green Chem. 2005, 7: 844 -
3c
Dupont J.Spencer J. Angew. Chem. Int. Ed. 2004, 43: 5296 -
4a
Katritzky AR.Singh S.Kirichenko K.Holbrey JD.Smiglak M.Reichert WM.Rogers RD. Chem. Commun. 2005, 868 -
4b
Fukumoto K.Yoshizawa M.Ohno H. J. Am. Chem. Soc. 2005, 127: 2398 -
4c
Carter EB.Culver SL.Fox PA.Goode RD.Ntai I.Tickell MD.Traylor RK.Hoffman NW.Davis JH. Chem. Commun. 2004, 630 -
4d
Keglevich G.Baan Z.Hermecz I.Novak T.Odinets IL. Curr. Org. Chem. 2007, 11: 107 -
5a
Imperato G.Eibler E.Niedermaier J.König B. Chem. Commun. 2005, 1170 -
5b
Imperato G.König B.Chiappe C. Eur. J. Org. Chem. 2007, 1049 - For reviews, see:
-
6a
Baudequin C.Baudoux J.Levillain J.Cahard D.Gaumont AC.Plaquevent JC. Tetrahedron: Asymmetry 2003, 14: 3081 -
6b
Ding J.Armstrong DW. Chirality 2005, 17: 281 -
6c
Baudequin C.Bregeon D.Levillain J.Guillen F.Plaquevent JC.Gaumont AC. Tetrahedron: Asymmetry 2005, 16: 3921 -
6d
Winkel A.Reddy PVG.Wilhelm R. Synthesis 2008, 999 -
6e
Bica K.Gaertner P. Eur. J. Org. Chem. 2008, 3235 -
6f
Headley AD.Ni B. Aldrichimica Acta 2007, 40: 107 -
6g
Ohno H.Fukumoto K. Acc. Chem. Res. 2007, 40: 1122 -
7a
Jurčík V.Gilani M.Wilhelm R. Eur. J. Org. Chem. 2006, 5103 -
7b
Jurčík V.Wilhelm R. Org. Biomol. Chem. 2005, 3: 239 -
7c
Jurčík V.Wilhelm R. Tetrahedron: Asymmetry 2006, 17: 801 -
7d
Clemens N.Sereda O.Wilhelm R. Org. Biomol. Chem. 2006, 4: 2285 - 8
Blanrue A.Wilhelm R. Synlett 2004, 2621 - For reviews, see:
-
9a
Nakayama J. J. Synth. Org. Chem. Jpn. 2002, 60: 106 -
9b
Kirmse W. Eur. J. Org. Chem. 2005, 237 -
10a
Nakayama J.Otani T.Sugihara Y.Ishii A. Tetrahedron Lett. 1997, 38: 5013 -
10b
Nakayma J.Akiyma I. J. Chem. Soc., Chem. Commun. 1992, 1522 -
10c
Nagasawa A.Akiyama I.Mashima S.Nakayama J. Heteroat. Chem. 1995, 6: 45 -
10d
Clemens DH.Bell AJ.O’Brien JL. Tetrahedron Lett. 1965, 6: 3257 -
10e
Winberg HE.Coffman DD. J. Am. Chem. Soc. 1965, 87: 2776 -
10f
Hansen J.Heinemann FW. Phosphorus Sulfur Silicon 1996, 118: 155 -
10g
Schössler W.Regitz M. Chem. Ber. 1974, 107: 1931 - 11
Krasuski W.Nikolaus D.Regitz M. Liebigs Ann. Chem. 1982, 1451 - 13
Coady DJ.Norris BC.Lynch VM.Bielawski W. Macromolecules 2008, 41: 3775 - 14
Reichardt C. Solvents and Solvent Effects in Organic Chemistry 3rd ed.: Wiley-VCH; Weinheim: 2003. - 15
Bennani Y.Hanessian S. Tetrahedron 1996, 52: 13837
References
For zwitterion 4, a yield of 80% was obtained. The procedure was not optimized for zwitterion 8.