Tytuł artykułu
Treść / Zawartość
Pełne teksty:
Identyfikatory
Warianty tytułu
Application of organic ionic liquids in polar [2+4] cycloaddition reactions
Języki publikacji
Abstrakty
Praca prezentuje możliwości wykorzystania organicznych cieczy jonowych jako mediów reakcyjnych dla polarnych [2+4] cykloaddycji.
The paper presents the possibility of using organic ionic liquids as reaction media for polar [2+4] cycloaddition.
Słowa kluczowe
Czasopismo
Rocznik
Tom
Strony
288--296
Opis fizyczny
Bibliogr. 62 poz., rys.
Twórcy
autor
- Instytut Ciężkiej Syntezy Organicznej ”Blachownia”, Kędzierzyn-Koźle
autor
- Centrum Technologii i Rozwoju, Azoty S.A., Tarnów
autor
- Zakład Chemii Organicznej, Politechnika Krakowska, Kraków
autor
- Instytut Ciężkiej Syntezy Organicznej „Blachownia”, Kędzierzyn-Koźle
autor
- Zakład Chemii Organicznej, Politechnika Krakowska, Kraków
Bibliografia
- 1. Pernak J.: Ciecze jonowe jako związki wielofunkcyjne. Przem. Chem. 2010, 89, 1499-1053.
- 2. Keskin S., Kayrak-Talay D., Akman U., Hortaçsu Ö.: A review of ionic liquids towards supercritical fluid applications. J. Supercrit. Fluids. 2007, 43, 150–180.
- 3. Yue C., Fang D., Liu L., Yi T-F.: Synthesis and application of task-specific ionic liquids used as catalysts and/or solvents in organic unit reactions. J. Mol. Liq. 2011, 163, 99–121.
- 4. Singh G., Kumar A.: Ionic liquids: Physico-chemical, solvent properties and their applications in chemical processes. Indian J. Chem. 2008, 47A, 459-503.
- 5. Ghandi K.: A Review of Ionic Liquids, Their Limits and Applications. Green Sust. Chem. 2014, 4, 44-53.
- 6. Hallett J.P., Welton T.: Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis 2. Chem. Rev. 2011, 111, 3508-3576.
- 7. Zhao D., Liu M., Zhang J., Li J., Ren P.: Synthesis, characterization, and properties of imidazole dicationic ionic liquids and their application in esterification. Chem. Eng. J. 2013, 221, 99-104.
- 8. Zhao Y., Li Z., Xia Ch.: Alkyl Sulfonate Functionalized Ionic Liquids: Synthesis, Properties, and Their Application in Esterification. Chinese J. Catal. 2011, 32, 440-445.
- 9. Wei Z., Li F., Xing H., Deng S., Ren Q.: Reactivity of Bronsted acid ionic liquids as dual solvent and catalyst for Fischer esterifications. Korean J. Chem. Eng. 2009, 26, 666-672.
- 10. Yinyin Y., Li H., Wenwen Z., Yu S., Ting C., Yunxiang Q., Zhenshan H.: Ionic Liquid Catalyzed the Internal Redox Esterification Reaction. Synth. Commun. 2013, 43, 1287-1298.
- 11. Gu Y., Shi F., Deng Y.: Esterification of aliphatic acids with olefin promoted by Brønsted acidic ionic liquids. J. Mol. Catal. A: Chem. 2004, 212, 71–75.
- 12. Aghabarari B., Dorostkar N., Ghiaci M., Amini S.G., Rahimi E., Martinez- Huerta M.V.: Esterification of fatty acids by new ionic liquids as acid catalysts. J Taiwan Inst, Chem. Eng. 2014, 45, 431–435.
- 13. Adams Ch.J., Earle M.J., Roberts G., Seddon K.R.: Friedel–Crafts reactions in room temperature ionic liquids. Chem. Commun. 1998, 2097-2098.
- 14. Liu Z.C., Meng X.H., Zhang R., Xu C.M.: Friedel-Crafts Acylation of Aromatic Compounds in Ionic Liquids. Pet. Sci. Technol. 2009, 27, 226-237.
- 15. Zhai C.P., Song A.X., Liu W.M.,. Wanga H.Q.: ESR Studies on a Friedel-Crafts Alkylation Reaction in [bmim]Cl-AlCl3 Ionic Liquid. J. Chin. Chem. Soc. 2006, 53, 887-890.
- 16. Tran P.H., Duus F. Le T.N.: Friedel–Crafts acylation using bismuth triflate in [BMI][PF6]. Tetrahedron Lett. 2012, 53, 222-224.
- 17. Valizadeh H., Vaghefi S.: One-Pot Wittig and Knoevenagel Reactions in Ionic Liquid as Convenient Methods for the Synthesis of Coumarin Derivatives. Synth. Commun. 2009, 39, 1666–1678.
- 18. Zicmanis A., Anteina L.: Dialkylimidazolium dimethyl phosphates as solvents and catalysts for the Knoevenagel condensation reaction. Tetrahedron Lett. 2014, 55, 2027-2028.
- 19. Potdar M.K., Rasalkar M.S., Mohile S.S., Salunkhe M.M.: Convenient and efficient protocols for coumarin synthesis via Pechmann condensation in neutral ionic liquids. J. Mol. Catal. A: Chem. 2005, 235, 249–252.
- 20. Khaligh N.G.: Synthesis of coumarins via Pechmann reaction catalyzed by 3-methyl- 1-sulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable acidic ionic liquid. Catal. Sci. Technol. 2012, 2, 1633-1636.
- 21. Nowakowska-Bogdan E., Dresler E.: Reakcje kondensacji fenoli z pirogronianem metylu w środowisku kwaśnej chloroglinianowej 1-n-butylo-3-metyloimidazoliowej cieczy jonowej. Przem. Chem. 2013, 92, 1868-1871.
- 22. Iglesias M., Gonzalez-Olmos R., Cota I., Medina F.: Brønsted ionic liquids: Study of physico-chemical properties and catalytic activity in aldol condensations. Chem. Eng. J. 2010, 162, 802-808.
- 23. Wang Ch., Liu J., Leng W., Gao Y.: Rapid and Efficient Functionalized Ionic Liquid-Catalyzed Aldol. Int. J. Mol. Sci. 2014, 15, 1284-1299.
- 24. Gui J., Deng Y., Hu Z., Sun Z.: A novel task-specific ionic liquid for Beckmann rearrangement: a simple and effective way for product separation. Tetrahedron Lett. 2004, 45, 2681-2683.
- 25. D., Jun-gang C., Da-peng L., Feng J., Han G., Xu-dong J. Ying-jie L.: Brønsted Acidic Ionic Liquids: Efficient and Recyclable Catalytic Systems for Beckmann Rearrangement. Chem. Res. Chin. Univ. 2011, 27, 973-976.
- 26. Zicmanis A., Katkevica S., Mekss P.: Lewis acid-catalyzed Beckmann rearrangement of ketoximes in ionic liquids. Catal. Commun. 2009, 10, 614–619.
- 27. Ma T., Feng R., Zou J., Zhang X., Wang L.: Ionic Liquid Catalytic Rearrangement of Polycyclic Hydrocarbons: A Versatile Route to Alkyl-Diamondoid Fuels. Ind. Eng. Chem. Res. 2013, 52, 2486–2492.
- 28. Priede E., Nakurte I., Zicmanis A.: Structure Effect of Imidazolium-Based Dicationic Ionic Liquids on Claisen Rearrangement. Synth. Commun. 2014, 44, 1803-1809.
- 29. McNulty J., Nair J.J., Robertson A., Lei A.: Efficient Carbonylation Reactions in Phosphonium Salt Ionic Liquids: Anionic Effects. Org. Lett. 2007, 9, 4575-4578.
- 30. Lapidus A.L., Eliseev O.L.: Catalytic carbonylation in ionic liquids. Solid Fuel Chem. 2010, 44, 197-202.
- 31. Choi Y.S., Shim Y.N., Lee J., Yoon J.H., Hong Ch.S., Cheong M. Kim H.S., Jang H G., Lee J.S.: Ionic liquids as benign catalysts for the carbonylation of amines to formamides. Appl. Catal., A., 2011, 404, 87– 92.
- 32. Yu B., Zhang H., Zhao Y., Chen S., Xu J., Hao L., Liu Z.: DBU-Based Ionic-Liquid-Catalyzed Carbonylation of o-Phenylenediamines with CO2 to 2-Benzimidazolones under Solvent-Free Conditions. ACS Catal., 2013, 3, 2076–2082.
- 33. Ryu J., Choi J.W., Suh D.J., Ahn D.J., Suh Y.W.: Dual catalytic function of 1,3-dialkylimidzolium halide ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural. Catal. Commun. 2012, 24, 11–15.
- 34. Chinnappan A., Jadhav A.H., Kim H., Chung W.J.: Ionic liquid with metal complexes: An efficient catalyst for selective dehydration of fructose to 5-hydroxymethylfurfural. Chem. Eng. J. 2014, 237, 95-100.
- 35. Muzart J.: Ionic Liquids as Solvents for Catalyzed Oxidations of Organic Compounds. Adv. Synth. Catal., 2006, 348, 275 – 295.
- 36. Kadokawa J.:”Ionic Liquids – New Aspects for the Future”. ISBN 2013, Chapter 14.
- 37. Shi Y.K., Qu G.F., Ping N., Zhang J., Feng H.: Advances of Application of Ionic Liquids in Catalytic Oxidation Reactions. Adv. Mater. Res. 2011, 233, 499-506.
- 38. Betz D., Altmann P., Cokoja M., Herrmann W.A., Kühn F.E.: Recent advances in oxidation catalysis using ionic liquids as solvents. Coord. Chem. Rev. 2011, 255,1518-154.
- 39. Kubisa P.: Application of ionic liquids as solvents for polymerization processes. Prog. Polym. Sci. 2004, 29, 3-1.
- 40. Strehmel V.: Ionic Liquids in Polymer Synthesis. Chem. Ing. Tech. 2011, 83, 1443-1453.
- 41. Kubisa P.: Ionic liquids as solvents for polymerization processes–Progress and Challenges . Prog. Polym. Sci. 2009, 34, 1333–1347.
- 42. Meng Z., Zheng X., Tang K., Liu J., Qin S.: Dissolution of natural polymers in ionic liquids: A review. e-Polymers 2012, 12, 317-345.
- 43. Gunaratne H. Q. N., Langrick C.R., Puga A.V., Seddon K.R., Whiston K.: Production of polyetheretherketone in ionic liquid media. Green Chem. 2013, 15, 1166–1172.
- 44. Jasiński R., Kwiatkowska M., Barański A.: Kinetics of the [4+2] cycloaddition of cyclopentadiene with (E)-2-aryl-1-cyano-1-nitroethenes. Monatsh. Chem. 2012, 143, 895-899.
- 45. Jasiński R., Kwiatkowska M., Barański A.: Stereoselectivity and kinetics of [4+2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes. J. Phys. Org. Chem. 2011, 24, 843-853.
- 46. Jasiński R., Kwiatkowska M., Barański A.: Mechanistyczne aspekty nieuzgodnionych (4+2)[pi]-elektronowych cykloaddycji. Wiad. Chem. 2007, 61, 485-514.
- 47. Mellor J.M., Webb C.F.: Stereochemistry of the Diels–Alder reaction: steric effects of the dienophile on endo-selectivity. J. Chem. Soc. Perkin. Trans 2. 1974, 17-22.
- 48. Fischer T., Sethi A., Welton T., Wolf J.: Diets-Alder Reactions in Room-Temperature Ionic Liquids. Tetrahedron Lett. 1999, 40, 793-796.
- 49. Vidiš A., Ohlin A., Laurenczy G., Küsters E., Sedelmeier G., Dyson P.J.: Rationalisation of Solvent Effects in the Diels-Alder Reaction Between Cyclopentadiene and Methyl Acrylate in Room Temperature Ionic Liquids. Adv. Synth. Catal. 2005, 347, 266-274.
- 50. Lee C.W.: Diels-Alder reactions in chloroaluminate ionic liquids: acceleration and selectivity enhancement. Tetrahedron Lett. 1999, 40, 2461-2464.
- 51. Srivastava V.: J. Chem. 2013, 1.
- 52. Stefaniak W., Janus E., Milchert E.: Diels–Alder Reaction of Cyclopentadiene and Alkyl Acrylates in the Presence of Pyrrolidinium Ionic Liquids with Various Anions. Catal. Lett. 2011, 141, 742-747.
- 53. Ludley P., Karodia N.: Phosphonium tosylates as solvents for the Diels-Alder reaction with 1,3-Cyclopentadiene. Arkivoc. 2002, 172-175.
- 54. Atherton J.C.C., Jones S.: Diels–Alder reactions of anthracene, 9-substituted anthracenes and 9,10-disubstituted anthracenes. Tetrahedron 2003, 59, 9039-9057.
- 55. Della-Rosa C., Ormachea C., Kneeteman M.N., Adam C., Mancini P.E.M.: Diels– Alder reactions of N-tosylpirroles developed in protic ionic liquids. Theoretical studies using DFT methods. Tetrahedron Lett. 2011, 52, 6754-6757.
- 56. Vafina G.F., Fazlyev R.R., Galin F.Z., Sprikhin L.V.: Ionic Liquid-Catalyzed Diels–Alder Reaction of Levopimaric Acid with Quinones. Russ. J. Org. Chem. 2009, 45, 500-504.
- 57. Van Buu O.N., Aupoix A., Vo-Thanh G.: Synthesis of novel chiral imidazoliumbased ionic liquids derived from isosorbide and their applications in asymmetric aza Diels–Alder reaction. Tetrahedron 2009, 65, 2260-2265.
- 58. Janus E., Bittner B.: Triethylsulfonium Bistriflimide as the Reaction Medium in Catalyzed and Uncatalyzed Cycloaddition [4 + 2]. Catal. Lett. 2010, 134, 147-154.
- 59. Janus E., Stefaniak W.: The Diels-Alder reaction in phosphonium ionic liquid catalysed by metal chlorides, triflates and triflimides. Catal. Lett. 2008, 124, 105-110.
- 60. Hayaki S., Kido K., Yokogawa D., Sato H., Sakaki S.: A theoretical analysis of a Diels-Alder reaction in ionic liquids. J. Phys. Chem. B. 2009, 113, 8227-8230.
- 61. Bittner B., Milchert E., Janus E.: Pat. PL 216790 B1.
- 62. Pernak J., Syguda A., Janus E.: Pat. PL 210989 B1.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-551bf2a3-c5da-4e2d-86ff-f3fcfba3d7a6