Methylated Imidazolinium-Dithiocarboxylates: Two Representatives of a New Class of Ionic Liquids

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.

ionic liquids - chirality - chiral cations - imidazolinium salts - zwitterions

References

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 

12

For zwitterion 4, a yield of 80% was obtained. The procedure was not optimized for zwitterion 8.

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