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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

Gleixner, Renate M., Joly, Kévin M., Tremayne, MaryJane, Kariuki, Benson, Male, Louise, Coe, Diane M. and Cox, Liam R. 2010. Reaction of 1,1'-Divinyl ferrocene with one-electron oxidants: entry into functionalised [4]ferrocenophanes and observation of an isotope-dependent chemoselectivity effect. Chemistry: A European Journal 16 (19) , pp. 5769-5777. 10.1002/chem.200903478

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Abstract

1,1′-Divinyl ferrocene (2) reacts with K3[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, [D2]-2 reacts to provide a diol-functionalised [4]ferrocenophane, [D2]-D/L-6 in addition to the expected keto-alcohol, [D1]-4. Variants on this one-electron oxidative cyclisation methodology can be used to give other [4]ferrocenophanes; thus, the reaction of 2 with CuCl2 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 [D2]-2 with K3[Fe(CN)6] are proposed.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: cyclization; cyclophanes; isotope effects; metallocenes
Publisher: Wiley
ISSN: 0947-6539
Last Modified: 04 Jun 2017 03:31
URI: http://orca-mwe.cf.ac.uk/id/eprint/22393

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