Redox-mediated reactions of vinylferrocene: Toward redox auxiliaries

Wiles, A. A. , Zhang, X., Fitzpatrick, B., Long, D.-L. , Macgregor, S. A. and Cooke, G. (2016) Redox-mediated reactions of vinylferrocene: Toward redox auxiliaries. Dalton Transactions, 45(17), pp. 7220-7225. (doi:10.1039/C6DT00875E) (PMID:27063914)

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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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Cooke, Professor Graeme and Wiles, Dr Alan and Fitzpatrick, Dr Brian and Long, Dr De Liang
Authors: Wiles, A. A., Zhang, X., Fitzpatrick, B., Long, D.-L., Macgregor, S. A., and Cooke, G.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Dalton Transactions
Publisher:Royal Society of Chemistry
ISSN:1477-9226
Published Online:11 April 2016
Copyright Holders:Copyright © 2016 Royal Society of Chemistry
First Published:First published in Dalton Transactions 45(17):7220-7225
Publisher Policy:Reproduced under a Creative Commons License
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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
445041Physical organic chemistry - opportunities in synthesis, materials and pharmaceuticalsGraeme CookeEngineering & Physical Sciences Research Council (EPSRC)EP/E036244/1CHEM - CHEMISTRY