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Synlett 2014; 25(17): 2447-2450
DOI: 10.1055/s-0034-1379018
DOI: 10.1055/s-0034-1379018
letter
When Chlorides are the Most Reactive: A Simple Route towards Diverse Mono- and Dicationic Dimethyl Phosphate Ionic Liquids
Further Information
Publication History
Received: 10 June 2014
Accepted after revision: 03 August 2014
Publication Date:
09 September 2014 (online)
Abstract
Structurally diverse aromatic and aliphatic ionic liquids have been prepared via anion metathesis utilizing alkylammonium chlorides and trimethyl phosphate. Excellent oxygen-containing functional-group tolerance in preparation of potentially greener dimethyl phosphate ionic liquids has been demonstrated. For the first time, this method has been employed in the synthesis of dicationic imidazolium-based ionic liquids possessing a dimethyl phosphate counterion, providing a simple, direct route towards structurally novel products of high purity.
Key words
monocationic ionic liquids - dicationic ionic liquids - anion metathesis - dimethyl phosphateSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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References
- 1a Hallett JP, Welton T. Chem. Rev. 2011; 111: 3508
- 1b Chatel G, Rogers RD. ACS Sustainable Chem. Eng. 2014; 2: 322
- 1c Plechkova NV, Seddon KR. Chem. Soc. Rev. 2008; 37: 123
- 1d Armand M, Endres F, MacFarlane DR, Ohno H, Scrosati B. Nat. Mater. 2009; 8: 621
- 2a Wang R, Jin C.-M, Twamley B, Shreeve JM. Inorg. Chem. 2006; 45: 6396
- 2b Anderson JL, Ding R, Ellern A, Armstrong DW. J. Am. Chem. Soc. 2005; 127: 593
- 2c Breitbach ZS, Armstrong DW. Anal. Bioanal. Chem. 2008; 390: 1605
- 2d Han X, Armstrong DW. Org. Lett. 2005; 7: 4205
- 2e Li X, Zhao D, Fei Z, Wang L. Sci. China Ser. B: Chem. 2006; 49: 385
- 2f Tang S, Baker GA, Zhao H. Chem. Soc. Rev. 2012; 41: 4030
- 3a Zhang ZC. WIREs Energy Environ. 2013; 2: 655 ; DOI: 10.1002/wene.67
- 3b Vitz J, Erdmenger T, Haensch C, Schubert US. Green Chem. 2009; 11: 417
- 3c Fukaya Y, Hayashi K, Wada M, Ohno H. Green Chem. 2008; 10: 44
- 3d Zhao D, Li H, Zhang J, Fu L, Liu M, Fu J, Ren P. Carbohydr. Polym. 2012; 87: 1490
- 3e Froschauer C, Hummel M, Laus G, Schottenberger H, Sixta H, Weber HK, Zuckerstätter G. Biomacromolecules 2012; 13: 1973
- 4a Zicmanis A, Anteina L. Tetrahedron Lett. 2014; 55: 2027
- 4b Zhang W, Xu W, Zhang F, Jin H, Wang Y, Li J. Res. Chem. Intermed. 2014; 40: 1337
- 4c Zhang S, Goncalves LD, Lefebvre H, Tessier M, Rousseau B, Fradet A. ACS Macro Lett. 2012; 1: 1079
- 4d Toräng J, Vanderheiden S, Nieger M, Bräse S. Eur. J. Org. Chem. 2007; 943
- 4e Mečiarová M, Toma Š, Kotrusz P. Org. Biomol. Chem. 2006; 4: 1420
- 5 Kuhlmann E, Himmler S, Giebelhaus H, Wasserscheid P. Green Chem. 2007; 9: 233
- 6a Ab Rani MA, Brant A, Crowhurst L, Dolan A, Lui M, Hassan NH, Hallett JP, Hunt PA, Niedermeyer H, Perez-Arlandis JM, Schrems M, Welton T, Wildinga R. Phys. Chem. Chem. Phys. 2011; 13: 16831
- 6b Bradaric CJ, Downard A, Kennedy C, Robertson AJ, Zhou Y. Green Chem. 2003; 5: 143
- 6c Harjani JR, Farrell J, Garcia MT, Singer RD, Scammells PJ. Green Chem. 2009; 11: 821
- 7a Chiappe C, Pieraccini D. J. Phys. Chem. A 2006; 110: 4937
- 7b Chiappe C, Pomelli CS, Rajamani S. J. Phys. Chem. B 2011; 115: 9653
- 8a Crowhurst L, Falcone R, Lancaster NL, Llopis-Mestre V, Welton T. J. Org. Chem. 2006; 71: 8847
- 8b Crowhurst L, Lancaster NL, Pérez-Arlandis JM, Welton T. J. Am. Chem. Soc. 2004; 126: 11549
- 8c Skrzypczak A, Neta P. Int. J. Chem. Kinet. 2004; 36: 253
- 8d Correia I, Welton T. Dalton Trans. 2009; 4115
- 9 Ignatyev NM, Welz-Biermann U, Kucheryna A, Willner H. WO 2006/063655 A1, 2006 ; Chem. Abstr. 2006, 145, 63041
- 10 Vu PD, Boydston AJ, Bielawski CW. Green Chem. 2007; 9: 1158
- 11 Froschauer C, Sixta H, Weber HK, Laus G, Kahlenberg V, Schottenberger H. Chem. Lett. 2012; 41: 945
- 12a Bara JE. Ind. Eng. Chem. Res. 2011; 50: 13614
- 12b Xiong Y, Wang H, Wu C, Wang R. Polym. Adv. Technol. 2012; 23: 1429
- 13a Omotowa BA, Shreeve JM. Organometallics 2004; 23: 783
- 13b Buitrago E, Tinnis F, Adolfsson H. Adv. Synth. Catal. 2012; 354: 217
- 13c Hummel M, Laus G, Schwärzler A, Bentivoglio G, Rubatscher E, Kopacka H, Wurst K, Kahlenberg V, Gelbrich T, Griesser UJ, Röder T, Weber HK, Schottenberger H, Sixta H In Cellulose Solvents: For Analysis, Shaping and Chemical Modification, ACS Symposium Series 1033. Liebert TF, Heinze TJ, Edgar KJ. American Chemical Society; Washington DC: 2010: 229
- 13d Wang Z, Li J, Wang H, Zhou G. Chem. Commun. 2013; 49: 9446
- 14a Biczak R, Pawlowska B, Balczewski P, Rychter P. J. Hazard. Mater. 2014; 274: 181
- 14b Wood N, Ferguson JL, Gunaratne HQ. N, Seddon KR, Goodacre R, Stephens GM. Green Chem. 2011; 13: 1843
- 15a Pham TP. T, Cho CW, Yun YS. Water Res. 2010; 44: 352
- 15b Stolte S, Matzke M, Arning J, Böschen A, Pitner WR, Welz-Biermann U, Jastorff B, Ranke J. Green Chem. 2007; 9: 1170
- 15c Matzke M, Stolte S, Thiele K, Juffernholz T, Arning J, Ranke J, Welz-Biermann U, Jastorff B. Green Chem. 2007; 9: 1198
- 16a Morrissey S, Pegot B, Coleman D, Garcia MT, Ferguson D, Quilty B, Gathergood N. Green Chem. 2009; 11: 475
- 16b Gathergood N, Scammells PJ. Aust. J. Chem. 2002; 55: 557
- 16c Garcia MT, Gathergood N, Scammells PJ. Green Chem. 2004; 6: 166
- 16d Petkovic M, Ferguson JL, Gunaratne HQ. N, Ferreira R, Leitão MC, Seddon KR, Rebelo LP. N, Pereira CS. Green Chem. 2010; 12: 643
- 17 Burrell AK, Del Sesto RE, Baker SN, McCleskeya TM, Baker GA. Green Chem. 2007; 9: 449