Formation of functionalized [3]ferrocenophane derivatives by an enamine condensation reaction

Journal of Organometallic Chemistry

Volumn 586, Issue 2, 1999, Pages 218-222

  Knüppel, Stephanie ^a   Fröhlich, Roland ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Dienamine formation; Enamine condensation reaction; Ferrocene; 3 Ferrocenophane synthesis

Indexed keywords

EID: 0038621241     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00274-0     Document Type: Article

References (31)

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11. For two formally related aldol examples see: (a) M. Sališova, Š. Toma, E. Solčániová, Coll. Czech. Chem. Commun. 45 (1980) 1290. (b) Y. Omote, R. Kobayashi, Y. Nakada, N. Sugiyama, Bull. Chem. Soc. Jpn. 46 (1973) 3315. For indications of a reversible intramolecular aldol coupling of 10 see: (c) C.R. Hauser, C.E. Cain, J. Org. Chem. 23 (1958) 1142. (d) C.E. Cain, T.A. Mashburn, C.R. Hauser, J. Org. Chem. 26 (1961) 1030. (e) C.R. Hauser, T.A. Mashburn, J. Org. Chem. 26 (1961) 1795.
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20. In contrast, Michael additions are frequently used to prepare [5]ferrocenophanes or larger ring systems. For examples see: (a) T.A. Mashburn, C.E. Cain, C.R. Hauser, J. Org. Chem. 25 (1960) 1982. (b) M. Furdik, Š. Toma, J. Suchy, P. Elecko, Chem. Zvesti, 15 (1961) 45. (c) Š. Toma, A. Gaplovsky, Coll. Czech. Chem. Commun. 47 (1983) 1988. (d) R. Dabard, H. Patin, Bull. Soc. Chim. Fr. (1973) 2158. (e) I.H. Barr, W.E. Watts, Tetrahedron 24 (1968) 3219.
21. In contrast, Michael additions are frequently used to prepare [5]ferrocenophanes or larger ring systems. For examples see: (a) T.A. Mashburn, C.E. Cain, C.R. Hauser, J. Org. Chem. 25 (1960) 1982. (b) M. Furdik, Š. Toma, J. Suchy, P. Elecko, Chem. Zvesti, 15 (1961) 45. (c) Š. Toma, A. Gaplovsky, Coll. Czech. Chem. Commun. 47 (1983) 1988. (d) R. Dabard, H. Patin, Bull. Soc. Chim. Fr. (1973) 2158. (e) I.H. Barr, W.E. Watts, Tetrahedron 24 (1968) 3219.
22. In contrast, Michael additions are frequently used to prepare [5]ferrocenophanes or larger ring systems. For examples see: (a) T.A. Mashburn, C.E. Cain, C.R. Hauser, J. Org. Chem. 25 (1960) 1982. (b) M. Furdik, Š. Toma, J. Suchy, P. Elecko, Chem. Zvesti, 15 (1961) 45. (c) Š. Toma, A. Gaplovsky, Coll. Czech. Chem. Commun. 47 (1983) 1988. (d) R. Dabard, H. Patin, Bull. Soc. Chim. Fr. (1973) 2158. (e) I.H. Barr, W.E. Watts, Tetrahedron 24 (1968) 3219.
23. In contrast, Michael additions are frequently used to prepare [5]ferrocenophanes or larger ring systems. For examples see: (a) T.A. Mashburn, C.E. Cain, C.R. Hauser, J. Org. Chem. 25 (1960) 1982. (b) M. Furdik, Š. Toma, J. Suchy, P. Elecko, Chem. Zvesti, 15 (1961) 45. (c) Š. Toma, A. Gaplovsky, Coll. Czech. Chem. Commun. 47 (1983) 1988. (d) R. Dabard, H. Patin, Bull. Soc. Chim. Fr. (1973) 2158. (e) I.H. Barr, W.E. Watts, Tetrahedron 24 (1968) 3219.
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25. Reviews: (a) Fe organic compounds, Gmelin Handbook of Inorganic Chemistry, 8th ed., vol. A8, Springer, Berlin, 1986. (b) B.W. Rockett, G. Marr, J. Organomet. Chem. 416 (1991) 327 and preceding annual reviews by these authors.
26. (a) S. Knüppel, G. Erker, R. Fröhlich, Angew. Chem. (1999), in press.
27. See also: (b) S.-D. Bai, X.-H. Wei, J.-P. Guo, D.-S. Liu, Z.-Y. Zhou, Angew. Chem. (1999), in press.
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31. See also: (b) A.N. Nesmeyanov, E.V. Leonova, N.S. Kochetkova, A.I. Malkova, J. Organomet. Chem. 96 (1975) 271.