NDLI: Reaction of 1,1′-Divinyl Ferrocene with One-Electron Oxidants: Entry into Functionalised [4]Ferrocenophanes and Observation of an Isotope-Dependent Chemoselectivity Effect

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Reaction of 1,1′-Divinyl Ferrocene with One-Electron Oxidants: Entry into Functionalised [4]Ferrocenophanes and Observation of an Isotope-Dependent Chemoselectivity Effect

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Reaction of 1,1′-Divinyl Ferrocene with One-Electron Oxidants: Entry into Functionalised [4]Ferrocenophanes and Observation of an Isotope-Dependent Chemoselectivity Effect

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Coe, Diane M. Gleixner, Renate M. Joly, Kévin M. Tremayne, Maryjane Male, Louise Kariuki, Benson M. Cox, Liam R.
Description	Author Affiliation: Gleixner RM ( School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK.)
Abstract	1,1′-Divinyl ferrocene (2) reacts with $K_{3}[Fe(CN)_{6}]$ under basic biphasic conditions to give a [4]ferrocenophane (4) in good yield. Incorporating deuterium labels into the internal positions of the vinyl groups of 2 affects the chemoselectivity of the reaction; thus under identical reaction conditions, $[D_{2}]-2$ reacts to provide a diol-functionalised [4]ferrocenophane, $[D_{2}]-D/L-6$ in addition to the expected keto-alcohol, $[D_{1}]-4.$ Variants on this one-electron oxidative cyclisation methodology can be used to give other [4]ferrocenophanes; thus, the reaction of 2 with $CuCl_{2}$ in MeOH or iPrOH leads to dialkoxy [4]ferrocenophanes 19 and 20, respectively, whereas the reaction of 2 with benzyl carbamate in the presence of tBuOCl gives a bis(carbamate)[4]ferrocenophane, 21. Mechanisms to account for the formation of the products, the stereoselectivity, and the unusual isotope-dependent chemoselectivity in the reaction of 2 and $[D_{2}]-2$ with $K_{3}[Fe(CN)_{6}]$ are proposed.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	19
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-05-17
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Ferrous Compounds Chemistry Isotopes Oxidants Vinyl Compounds Electrochemistry Electrons Molecular Structure Oxidation-Reduction Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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