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

Max Roemer; Duncan A. Wild; Brian W. Skelton; Alexandre N. Sobolev; Gareth L. Nealon; Matthew J. Piggott; George A. Koutsantonis

doi:10.1039/c7dt02037f

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

Max Roemer^*, Duncan A. Wild, Brian W. Skelton, Alexandre N. Sobolev, Gareth L. Nealon, Matthew J. Piggott, George A. Koutsantonis

^*Corresponding author for this work

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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.

Original language	English
Pages (from-to)	10899-10907
Number of pages	9
Journal	Dalton Transactions
Volume	46
Issue number	33
DOIs	https://doi.org/10.1039/c7dt02037f
Publication status	Published - 7 Sep 2017
Externally published	Yes

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Copyright the Publisher 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

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title = "Control over cyclisation sequences of 1,1′-bifunctional octamethylferrocenes to ferrocenophanes",

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.",

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AU - Roemer, Max

AU - Wild, Duncan A.

AU - Skelton, Brian W.

AU - Sobolev, Alexandre N.

AU - Nealon, Gareth L.

AU - Piggott, Matthew J.

AU - Koutsantonis, George A.

N1 - Copyright the Publisher 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

PY - 2017/9/7

Y1 - 2017/9/7

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AB - 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.

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

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