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.

Original languageEnglish
Pages (from-to)10899-10907
Number of pages9
JournalDalton Transactions
Volume46
Issue number33
DOIs
Publication statusPublished - 2017

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Sodium Hydroxide
Cyclization
Discrete Fourier transforms
Electrons

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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.",
author = "Max Roemer and Wild, {Duncan A.} and Skelton, {Brian W.} and Sobolev, {Alexandre N.} and Nealon, {Gareth L.} and Piggott, {Matthew J.} and Koutsantonis, {George A.}",
year = "2017",
doi = "10.1039/c7dt02037f",
language = "English",
volume = "46",
pages = "10899--10907",
journal = "Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry",
issn = "1477-9226",
publisher = "ROYAL SOC CHEMISTRY",
number = "33",

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TY - JOUR

T1 - Control over cyclisation sequences of 1,1′-bifunctional octamethylferrocenes to ferrocenophanes

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.

PY - 2017

Y1 - 2017

N2 - 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.

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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U2 - 10.1039/c7dt02037f

DO - 10.1039/c7dt02037f

M3 - Article

VL - 46

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EP - 10907

JO - Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry

JF - Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry

SN - 1477-9226

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ER -