全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

Ligand Exchange Reaction of Ferrocene with Substituted Benzenes

DOI: 10.4236/ijoc.2022.121001, PP. 1-10

Keywords: Ferrocene, Ligand Exchange Reaction, Substituted Benzenes

Full-Text   Cite this paper   Add to My Lib

Abstract:

Ligand exchange reaction is one of the typical reactions of ferrocene. In this paper, ligand exchange reactions were carried out between ferrocene and various substituted benzenes using aluminum chloride catalysis. The product yields of the reactions with alkanoyl- and alkoxybenzenes were low because of the coordination of aluminum chloride to the oxygens of the benzene substituents. Comparing the reactions using o- and p-dimethoxybenzene, the former was revealed to be less reactive; this is likely due to the deviation of the π-electrons of its benzene ring being larger.

References

[1]  Kealy, T.J. and Pauson, P.L. (1951) A New Type of Organo-Iron Compound. Nature, 168, 1039-1040.
https://doi.org/10.1038/1681039b0
[2]  Miller, S.A., Tebboth, J.A. and Tremaine, J.F. (1952) Dicyclopentadienyliron. Journal of Chemical Society, 632-635.
https://doi.org/10.1039/jr9520000632
[3]  Nesmeyanov, A.N., Vol’kenau, N.A. and Isaeva, L.S. (1963) The Interaction of Ferrocene and Its Derivatives with Aromatic Compounds. Tetrahedron Letters, 4, 1725-1729.
https://doi.org/10.1016/S0040-4039(01)90903-7
[4]  Astruc, D. and Dabard, R. (1976) Contribution to the Study of Metallocenes: XXIV. on the Mechanism of Ligand Exchange and Complexation by Aluminum Chloride of Ferrocene and Its Alkylated and Acylated Derivatives. Journal of Organometallic Chemistry, 111, 339-347.
https://doi.org/10.1016/S0022-328X(00)98142-7
[5]  Abd-El-Aziz, A.S. and Bernardin, S. (2000) Synthesis and Reactivity of Arenes Coordinated to Cyclopentadienyliron Cations. Coordination Chemistry Reviews, 203, 219-267.
https://doi.org/10.1016/S0010-8545(99)00182-4
[6]  Astruc, D. and Dabrd, R. (1976) Organo-Iron Complexes of Aromatic Compounds. Applications in Synthesis. Tetrahedron, 39, 4027-4095.
https://doi.org/10.1016/S0040-4020(01)88627-0
[7]  Hayashi, T., Okada, Y. and Shimizu, S. (1996) Studies on Ferrocene Derivatives. Part 12. Substituent Effects for the Disproportionation, Synproportionation and Ligand Exchange Reactions of t-Butylferrocenes. Transition Metal Chemistry, 21, 418-422.
https://doi.org/10.1007/BF00140783
[8]  Okada, Y., Huruya, H. and Imori, Y. (2015) Ligand Exchange Reaction of Ferrocene with Heterocycles. International Journal of Organic Chemistry, 5, 282-290.
https://doi.org/10.4236/ijoc.2015.54028
[9]  Okada, Y., Yoshigami, Y. and Hayashi, T. (2003) Studies on Ferrocene Derivatives. Part XVI. Steric Effects on the Ligand Exchange Reactions of Alkylferrocenes. Transition Metal Chemistry, 28, 794-799.
https://doi.org/10.1023/A:1026006314010
[10]  Vela, J., Vaddadi, S., Cundari, T.R., Smith, J.M., Gregory, E.A., Lachicotte, R.J., Flaschenriem, C.J. and Holland, P.L. (2004) Reversible Beta-Hydrogen Elimination of Three-Coordinate Iron(II) Alkyl Complexes: Mechanistic and Thermodynamic Studies. Organometallics, 23, 5226-5239.
https://doi.org/10.1021/om049415+

Full-Text

Contact Us

[email protected]

QQ:3279437679

WhatsApp +8615387084133