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Updated: Mar 22, 2026

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
Published on: October 18, 2018
Redox-mediated reactions of vinylferrocene: toward redox auxiliaries
Alan A Wiles1, Xiaolu Zhang, Brian Fitzpatrick
1Glasgow Centre for Physical Organic Chemistry, WestCHEM, School of Chemistry, University of Glasgow, Glasgow, G12 8QQ, UK. graeme.cooke@glasgow.ac.uk.
Abstract:
Chemical redox reactions have been exploited to transform unreactive vinylferrocene into a powerful dienophile for the Diels-Alder reaction and reactive substrate for thiol addition reactions upon conversion to its ferrocenium state. We have further investigated the ability of these reactions to facilitate redox-auxiliary-like reactivity by further hydrogenolyisis of the Diels-Alder adduct to the corresponding cyclopentane derivative.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.