Novel Isothiocyanato Esters Appended to Task-Specific Ionic Liquid as New Tools For Ionic Liquid Phase Organic Synthesis (IoLiPOS)

Abstract

The synthesis of isothiocyanato esters appended to (polyethylene glycol)-ionic liquid phases is reported. The starting task-specific ionic liquids (TSILs) were functionalized in good yields with bromoacetic acid or 4-chlorobutyroyl chloride by usual esterification reaction conditions. In the second step, the isocyanato esters appended to TSILs were obtained by displacement with potassium thiocyanate in refluxing anhydrous MeCN. The isothiocyanato-TSILs were characterized by NMR (¹H, ¹³C), mass spectrometry (MS) and IR spectroscopy.

Key words

task-specific ionic liquid - isothiocyanato ester - ionic liquid phase

References

• 1 Ionic Liquids in Synthesis   Wasserscheid P. Welton T. Wiley-VCH; Weinheim, Germany: 2003. 
• Reviews on ionic liquid, see:
• 2a Wasserscheid P. Keim W. Angew. Chem. Int. Ed.  2000,  39:  3773 
• 2b Dupont J. de Souza RF. Suarez PAZ. Chem. Rev.  2002,  102:  3667 
• 2c Welton T. Chem. Rev.  1999,  99:  3667 
• 2d Gordon CM. Appl. Catal. A  2001,  222:  101 
• 2e Olivier-Bourbigou H. Magna L. J. Mol. Catal. A: Chem.  2002,  182-183:  419 
• 3 Buijsman R. Van Vuuren E. Sterrenburg JG. Org. Lett.  2001,  3:  3785 
• 4 Visser AE. Swatloski RP. Reichert MW. Mayton R. Sheff S. Wierzbicki A. Davis J. Rogers RD. Chem. Commun.  2001,  135 
• 5a Baleizao C. Gigante B. Garcia H. Carma A. Tetrahedron Lett.  2003,  44:  6813 
• 5b Audic C. Clavier H. Mauduit M. Guillemin JC. J. Am. Chem. Soc.  2003,  125:  9248 
• 6 Bates ED. Mayton RD. Ntai I. Davies JH. J. Am. Chem. Soc.  2002,  124:  926 
• 7 Fraga-Dubreuil J. Bourhala K. Rahmouni M. Bazureau JP. Hamelin J. Cat. Commun.  2002,  3:  185 
• 8 Fraga-Dubreuil J. Bazureau JP. Tetrahedron Lett.  2001,  42:  6097 
• 9 de Kort M. Tuin AW. Kuiper S. Overklecft HS. Vander Marel GA. Buijsman RC. Tetrahedron Lett.  2004,  45 
• 10 Miao W. Chan TH. Org. Lett.  2003,  5:  5003 
• 11 Anjaiah S. Chandrasekhar S. Grée R. Tetrahedron Lett.  2004,  45:  569 
• 12 Fraga-Dubreuil J. Bazureau JP. Tetrahedron  2003,  59:  6121 
• 13 Hakkou H. Vanden Eynde JJ. Bazureau JP. Hamelin J. Tetrahedron  2004,  60:  3745 
• For review, see:
• 14a Berlinck RGS. Fortschr. Chem. Org. Naturst.  1995,  66:  119 
• 14b Berlinck RGS. Nat. Prod. Rep.  1996,  13:  377 
• 15 Chérouvrier JR. Carreaux F. Bazureau JP. Tetrahedron Lett.  2002,  43:  3581 
• 16 Guanidino Compounds in Biology and Medecine   De Deyn P. Marescau B. Qureshi IA. Mori A. John Libbey; London: 1997. 
• 17 Fraga-Dubreuil J. Famelart MH. Bazureau JP. Org. Process. Res. Dev.  2002,  6:  374 
• 18 Seddon KR. Stark A. Torres MJ. Pure Appl. Chem.  2000,  72:  2275 
• 19 Vogel AI. A Textbook of Quantitative Inorganic Analysis   3rd ed:  Longmans, Green and Co; London: 1961. 
• 20a Stradler A. Kappe CO. Tetrahedron  2001,  57:  3915 
• 20b Mathias LJ. Synthesis  1979,  561 
• 21 Scriven EFV. Chem. Soc. Rev.  1983,  12:  129 
• 22 Wilson LJ. Klopfenstein SR. Li M. Tetrahedron Lett.  1999,  40:  3999