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Issue 33, 2017
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Control over cyclisation sequences of 1,1′-bifunctional octamethylferrocenes to ferrocenophanes

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Abstract

This paper describes the facile synthesis of a number of electron rich octamethyl[1.4]ferrocenophanes with unsaturated handles from 1,1′-bis(1-chlorovinyl)octamethylferrocene. Treatment of this reactive compound with sodium hydroxide in DMF initiates a series of reactions resulting in the formation of four different ferrocenophanes. The most complex of these products arises from a cascade of cyclisations giving an unusual, unsymmetrical bis-ferrocenophane with a central fused cyclobutene. Control over the reaction outcome is achieved by manipulating the concentration of NaOH. Mechanisms are proposed, and supported by DFT calculations.

Graphical abstract: Control over cyclisation sequences of 1,1′-bifunctional octamethylferrocenes to ferrocenophanes

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Publication details

The article was received on 05 Jun 2017, accepted on 18 Jul 2017 and first published on 20 Jul 2017


Article type: Paper
DOI: 10.1039/C7DT02037F
Citation: Dalton Trans., 2017,46, 10899-10907
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    Control over cyclisation sequences of 1,1′-bifunctional octamethylferrocenes to ferrocenophanes

    M. Roemer, D. A. Wild, B. W. Skelton, A. N. Sobolev, G. L. Nealon, M. J. Piggott and G. A. Koutsantonis, Dalton Trans., 2017, 46, 10899
    DOI: 10.1039/C7DT02037F

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