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.
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References
H.S.P. Rao S. Jothilingam (2001) Tetrahedron Lett. 42 6595 Occurrence Handle10.1016/S0040-4039(01)01793-2
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
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
J.P. Boukou-Poba M. Farnier R. Guilard (1979) Tetrahedron Lett. 19 1717 Occurrence Handle10.1016/S0040-4039(01)93634-2
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
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
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
D. Dhanak, C.B. Reese, S. Romana and G. Zappia, J. Chem. Soc., Chem. Commun. (1986) 903
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
B. Sezen D. Sames (2003) J. Am. Chem. Soc. 125 5274 Occurrence Handle1:CAS:528:DC%2BD3sXivVCltr4%3D Occurrence Handle10.1021/ja034848+
H. Adkins L.G. Lundsted (1949) J. Am. Chem. Soc. 71 2964 Occurrence Handle1:CAS:528:DyaG3MXjsFeg Occurrence Handle10.1021/ja01177a004
S. Wawzonek G.R. Hansen (1966) J. Org. Chem. 31 3580 Occurrence Handle1:CAS:528:DyaF2sXisVCk
C.F.H. Allen C.V. Wilson (1955) Org. Synth. Coll. III 358
M.P. Sammes M.W.L. Chung A.R. Katritzky (1985) J. Chem. Soc. Perkin Trans. 1 1773 Occurrence Handle10.1039/p19850001773
T. Lakhlifi A. Sedqui T. Fathi B. Laude J.-F. Robert (1994) Can. J. Chem. 6 1417 Occurrence Handle10.1139/v94-178
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
H. Rapoport N. Castagnoli SuffixJr (1962) J. Am. Chem. Soc. 84 2178 Occurrence Handle1:CAS:528:DyaF38XktlKhsLs%3D Occurrence Handle10.1021/ja00870a032
U. Burger F. Dreier (1980) Helv. Chim. Acta 63 1190 Occurrence Handle1:CAS:528:DyaL3MXosVSjtQ%3D%3D Occurrence Handle10.1002/hlca.19800630510
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
N.I. Schuikin T.I. Naryschkina (1961) J. Prakt. Chem. 13 183 Occurrence Handle10.1002/prac.19610130310
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
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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
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DOI: https://doi.org/10.1007/s10562-006-0151-6