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Catalytic Potential of a New Polymer-Anchored Multisite Phase Transfer Catalyst in the Dichlorocarbene Addition to Indene

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Abstract

The popularity of triphase catalysis in industries is due to straightforward catalyst recovery from reaction mixture. In this work we report a facile preparation a new polymer-anchored multisite phase transfer catalyst viz., polymer-anchored-2-benzyl-2-phenyl-1,3-bis(triethylmethylene ammonium chloride) (PABPBTAC) using polystyrene-based cross-linked beads. In order to ascertain the catalytic efficiency of the new heterogeneous catalyst, we studied its catalytic activity in the conversion of indene into dichlorocyclopropyl indene using chloroform and sodium hydroxide. Comparative catalytic efficiency of the new polymer-anchored multisite phase transfer catalyst with polymer-supported single site onium salts revealed that the new heterogeneous phase transfer catalyst is highly active than others. Further, from the influence of variation of experimental parameters, such as [substrate], [catalyst], [NaOH], stirring speed and temperature on indene conversion was studied in detail.

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References

  1. Menger FM (1972) Chem Soc Rev 1:229

    Article  CAS  Google Scholar 

  2. Jarrouse JCR (1951) Hebd Seances Acad Sci Ser C 232:1424

    Google Scholar 

  3. Akelah A, Moet A (1990) Functionalized polymers and their applications. Chapman and Hall, New York

    Google Scholar 

  4. Hodge P, Sherington DC (1988) Synthesis and separations using functionalized polymers. Wiley, New York

    Google Scholar 

  5. Kiasa AR, Badri R, Zargar B, Sayyahi S (2008) J Org Chem 73:8382

    Article  Google Scholar 

  6. Hermkens PHH, Ottenhejm HCJ, Rees D (1996) Tetrahedron 52:4527

    Article  CAS  Google Scholar 

  7. Thomson LA, Ellmann JA (1996) Chem Rev 96:555

    Article  Google Scholar 

  8. Desikan S, Doraiswany LK (1995) Ind Eng Chem Res 34:3524

    Article  CAS  Google Scholar 

  9. Regen SL (1975) J Am Chem Soc 97:5956

    Article  CAS  Google Scholar 

  10. Dehmlow EV, Dehmlow SS (1993) Phase transfer catalysis. Verlag Chemie, Weinheim

    Google Scholar 

  11. Starks CM, Liotta CL, Halpern M (1994) Phase-transfer catalysis, fundamentals, applications, and industrial perspectives. Chapman and Hall, New York

    Google Scholar 

  12. Weber WP, Gokel GW (1977) Phase transfer catalysis organic synthesis. Springer-Verlag, New York

    Google Scholar 

  13. Regen SL (1976) J Am Chem Soc 98:6270

    Article  CAS  Google Scholar 

  14. Regen SL, Besse JJ (1979) J Am Chem Soc 101:4059

    Article  CAS  Google Scholar 

  15. Tomoi M, Ford WT (1981) J Am Chem Soc 103:3828

    Article  CAS  Google Scholar 

  16. Ragaini V, Colombo G, Barzhagi P (1988) Ind Eng Chem Res 27:1382

    Article  CAS  Google Scholar 

  17. Schlunt P, Chau PC (1986) J Catal 102:348

    Article  CAS  Google Scholar 

  18. Arrad O, Sasson Y (1990) J Org Chem 55:2952

    Article  CAS  Google Scholar 

  19. Ford WT, Lee J, Tomoi M (1982) Macromolecules 15:1246

    Article  CAS  Google Scholar 

  20. Tundo P, Venturello P, Angeletti E (1982) J Am Chem Soc 104:6551

    Article  CAS  Google Scholar 

  21. Naik SD Doraiswamy LK (1999) AIChE J 612

  22. Balakrishnan T, Haribabu S, Perumal A (1990) J Polym Science Part A: Poly Chem 28:1421

    Article  CAS  Google Scholar 

  23. Tamami B, Mahdavi H (2002) Tetrahedron Lett 43:6225

    Article  CAS  Google Scholar 

  24. Wu HS, Lee CS (2001) J Catal 199:217

    Article  CAS  Google Scholar 

  25. Annunziata R, Benaglia M, Cinquini M, Cozzi F, Tocco G (2000) Org Lett 2:1737

    Article  CAS  Google Scholar 

  26. Brown JM, Jenkins JA (1976) J Chem Soc Chem Commun 458

  27. Montanari F, Tundo P (1981) J Org Chem 46:2125

    Article  CAS  Google Scholar 

  28. Ford WT, Balakrishnan T (1981) Macromolecules 54:575

    Google Scholar 

  29. Ford WT, Yacoub SA (1981) J Org Chem 48:1029

    Google Scholar 

  30. Balakrishnan T, Ford WT (1982) J Appl Polym Sci 27:133

    Article  CAS  Google Scholar 

  31. Balakrishnan T, Ford WT (1983) J Org Chem 48:1029–1035

    Article  CAS  Google Scholar 

  32. Ohtani N, Wilkie CA, Nigam A, Regen SL (1981) Macromolecules 14:516

    Article  CAS  Google Scholar 

  33. Benaglia M, Puglisi A, Cozzi F (2003) Chem Rev 103:3401

    Article  CAS  Google Scholar 

  34. Thierry B, Plaquevent JC, Cahard D (2001) Tetrahedron Asymmetr 12:983

    Article  CAS  Google Scholar 

  35. Zeng QL, Weng W, Jiang YZ (2001) Chemistry 69:547

    Google Scholar 

  36. Chinchilla R, Mazon P, Najera C (2000) Tetrahedron Asymmetr 11:3227

    Article  Google Scholar 

  37. Idoux JP, Wysocki R, Young S, Turcot J, Ohlman C, Leonard R (1983) Synth Commun 13:139

    Article  CAS  Google Scholar 

  38. Balakrishnan T, Jayachandran JP (1995) J Chem Soc Perkin Trans 2:2081

    Google Scholar 

  39. Balakrishnan T, Jayachandran JP (1995) Synth Commun 25:3821

    Article  CAS  Google Scholar 

  40. Benaglia M, Cinquini M, Cocci F, Tocco G (2002) Tetrahedron Lett 43:3391

    Article  CAS  Google Scholar 

  41. Balakrishnan T, Murugan E (2003) J Poly Sci Part A: Poly Chem 42:347

    Article  Google Scholar 

  42. Chou SC, Weng HS (1990) J Appl Poly Sci 39:1665

    Article  CAS  Google Scholar 

  43. Tomoi M, Ford WT (1980) J Am Chem Soc 102:714

    Article  Google Scholar 

  44. Rabonivitz M, Sasson Y, Halpern M (1983) J Org Chem 48:1022

    Article  Google Scholar 

  45. Reeves WP, Hilbrich RG (1976) Tetrahedron 32:2235

    Article  CAS  Google Scholar 

  46. Starks CM, Owens RM (1973) J Am Chem Soc 95:3613

    Article  CAS  Google Scholar 

  47. Balakrishnan T, Ford WT (1981) Tetrahedron Lett 4377

  48. Rajendran V, Wang ML (2008) J Mol Catal A: Chem 23:288

    Google Scholar 

  49. Helfferich F (1962) Ion exchange. McGraw Hill, New York

    Google Scholar 

  50. Jayachandran JP, Balakrishnan T, Wang ML, Mol J (2000) Catal A: Chem 152:91

    Article  CAS  Google Scholar 

  51. Tomoi M, Ford WT (1981) J Am Chem Soc 103:3821

    Article  CAS  Google Scholar 

  52. Halpern M, Sasson Y, Rabinovitz M (1984) J Org Chem 49:2011

    Article  CAS  Google Scholar 

  53. Sasson Y, Bilman N (1984) J Chem Soc Perkin Trans 2:2029

    Google Scholar 

  54. Balakrishnan T, Murugan E, Siva A (2004) App Cat A: Gen 273:89

    Article  CAS  Google Scholar 

  55. Regen SL, Bolikal D, Barcelon C (1981) J Org Chem 46:2511

    Article  CAS  Google Scholar 

  56. Molinary H, Montanary F, Quisci S, Tundo P (1979) J Am Chem Soc 101:3920

    Article  Google Scholar 

  57. Landini D, Maia A, Rampoldi A (1986) J Org Chem 51:5475

    Article  CAS  Google Scholar 

  58. Makosza M, Bialecka E (1977) Tetrahedron Lett 18:183

    Article  Google Scholar 

  59. Chiellini E, Solaro R, Antone SD (1980) J Org Chem 45:4179

    Article  Google Scholar 

  60. Halpern M, Sasson Y, Rabinovitz M (1982) Tetrahedron 38:3183

    Article  CAS  Google Scholar 

  61. Balakrishnan T, Shabeer TK, Nellie K (1991) Proc Indian Acad Sci (Chem Sci) 103:785

    CAS  Google Scholar 

  62. Murugan E, Gopinath P (2007) Appl Catal A: Gen 319:72

    Article  CAS  Google Scholar 

Download references

Acknowledgments

One of the authors (VA) is thankful to Dr. E. Murugan, Reader, Department of Physical Chemistry, University of Madras, for his constant encouragement. Financial assistance for one of the authors (VA) from University of Madras is gratefully acknowledged.

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Correspondence to P. A. Vivekanand.

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Vivekanand, P.A., Balakrishnan, T. Catalytic Potential of a New Polymer-Anchored Multisite Phase Transfer Catalyst in the Dichlorocarbene Addition to Indene. Catal Lett 131, 587–596 (2009). https://doi.org/10.1007/s10562-009-0019-7

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  • DOI: https://doi.org/10.1007/s10562-009-0019-7

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