Skip to main content
Log in

Aromatisation of 2-phenyl-1-pyrroline to 2-phenylpyrrole using activated carbon

  • Published:
Catalysis Letters Aims and scope Submit manuscript

2-phenyl-1-pyrroline was selectively dehydrogenated to 2-phenylpyrrole using activated carbon. Aromatisation reactions were performed using toluene at reflux. Only 30 min were sufficient for the dehydrogenation to occur. Maximum conversion values were obtained at ca. 98%, corresponding to maximum yields of 2-phenylpyrrole of ca. 45%. The final product showed high purity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. H.S.P. Rao S. Jothilingam (2001) Tetrahedron Lett. 42 6595 Occurrence Handle10.1016/S0040-4039(01)01793-2

    Article  Google Scholar 

  2. R.U. Braun K. Zeitler T.J.J Müller (2001) Org. Lett. 3 3297 Occurrence Handle1:CAS:528:DC%2BD3MXmvVSgtbY%3D Occurrence Handle10.1021/ol0165185

    Article  CAS  Google Scholar 

  3. C.E. Hewton M.C. Kimber D.K. Taylor (2002) Tetrahedron Lett. 43 3199 Occurrence Handle1:CAS:528:DC%2BD38XivVOktr8%3D Occurrence Handle10.1016/S0040-4039(02)00503-8

    Article  CAS  Google Scholar 

  4. J.P. Boukou-Poba M. Farnier R. Guilard (1979) Tetrahedron Lett. 19 1717 Occurrence Handle10.1016/S0040-4039(01)93634-2

    Article  Google Scholar 

  5. S.A. Burns R.J.P. Corriu V.H. Huynh J.J.E. Moreau (1987) J. Organomet. Chem. 333 281 Occurrence Handle1:CAS:528:DyaL1cXlt12is78%3D Occurrence Handle10.1016/S0022-328X(00)99805-X

    Article  CAS  Google Scholar 

  6. G.J. Ellames C.T. Hewkin R.F.W. Jackson D.I. Smith S.P. Standen (1989) Tetrahedron Lett. 26 3471 Occurrence Handle10.1016/S0040-4039(00)99275-X

    Article  Google Scholar 

  7. W. Saal Particlevon der R. Reinhardt J. Stawitz H. Quast (1998) Eur. J. Org. Chem. 8 1645 Occurrence Handle10.1002/(SICI)1099-0690(199808)1998:8<1645::AID-EJOC1645>3.0.CO;2-H

    Article  Google Scholar 

  8. D. Dhanak, C.B. Reese, S. Romana and G. Zappia, J. Chem. Soc., Chem. Commun. (1986) 903

  9. L. Filippini M. Gusmeroli R. Riva (1992) Tetrahedron. Lett. 33 1755 Occurrence Handle1:CAS:528:DyaK38XltFWns7Y%3D Occurrence Handle10.1016/S0040-4039(00)91725-8

    Article  CAS  Google Scholar 

  10. B. Sezen D. Sames (2003) J. Am. Chem. Soc. 125 5274 Occurrence Handle1:CAS:528:DC%2BD3sXivVCltr4%3D Occurrence Handle10.1021/ja034848+

    Article  CAS  Google Scholar 

  11. H. Adkins L.G. Lundsted (1949) J. Am. Chem. Soc. 71 2964 Occurrence Handle1:CAS:528:DyaG3MXjsFeg Occurrence Handle10.1021/ja01177a004

    Article  CAS  Google Scholar 

  12. S. Wawzonek G.R. Hansen (1966) J. Org. Chem. 31 3580 Occurrence Handle1:CAS:528:DyaF2sXisVCk

    CAS  Google Scholar 

  13. C.F.H. Allen C.V. Wilson (1955) Org. Synth. Coll. III 358

    Google Scholar 

  14. M.P. Sammes M.W.L. Chung A.R. Katritzky (1985) J. Chem. Soc. Perkin Trans. 1 1773 Occurrence Handle10.1039/p19850001773

    Article  Google Scholar 

  15. T. Lakhlifi A. Sedqui T. Fathi B. Laude J.-F. Robert (1994) Can. J. Chem. 6 1417 Occurrence Handle10.1139/v94-178

    Article  Google Scholar 

  16. A. Padwa J.R. Gasdaska M. Tomas N.J. Turro Y. Cha I.R. Gould (1986) J. Am. Chem. Soc. 108 6739 Occurrence Handle1:CAS:528:DyaL28XlslWmtrc%3D Occurrence Handle10.1021/ja00281a046

    Article  CAS  Google Scholar 

  17. H. Rapoport N. Castagnoli SuffixJr (1962) J. Am. Chem. Soc. 84 2178 Occurrence Handle1:CAS:528:DyaF38XktlKhsLs%3D Occurrence Handle10.1021/ja00870a032

    Article  CAS  Google Scholar 

  18. U. Burger F. Dreier (1980) Helv. Chim. Acta 63 1190 Occurrence Handle1:CAS:528:DyaL3MXosVSjtQ%3D%3D Occurrence Handle10.1002/hlca.19800630510

    Article  CAS  Google Scholar 

  19. L.C. Craig H. Bulbrook R.M. Hixon (1931) J. Am. Chem. Soc. 53 1831 Occurrence Handle1:CAS:528:DyaA3MXislSgtA%3D%3D Occurrence Handle10.1021/ja01356a028

    Article  CAS  Google Scholar 

  20. N.I. Schuikin T.I. Naryschkina (1961) J. Prakt. Chem. 13 183 Occurrence Handle10.1002/prac.19610130310

    Article  Google Scholar 

  21. A. Burghart H. Kim M.B. Welch L.H. Thoresen J. Reibenspies K. Burgess F. Bergström L.B.-A. Johansson (1999) J. Org. Chem. 64 7813 Occurrence Handle1:CAS:528:DyaK1MXmt12lt7w%3D Occurrence Handle10.1021/jo990796o

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Pedro T. Gomes.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Carabineiro, S.A., Bellabarba, R.M., Gomes, P.T. et al. Aromatisation of 2-phenyl-1-pyrroline to 2-phenylpyrrole using activated carbon. Catal Lett 111, 221–225 (2006). https://doi.org/10.1007/s10562-006-0151-6

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-006-0151-6

Keywords

Navigation