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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