Redox-mediated reactions of vinylferrocene: Toward redox auxiliaries

Alan A. Wiles; Xiaolu Zhang; Brian Fitzpatrick; De Liang Long; Stuart A. Macgregor; Graeme Cooke

doi:10.1039/c6dt00875e

Redox-mediated reactions of vinylferrocene: Toward redox auxiliaries

Alan A. Wiles
, Xiaolu Zhang
, Brian Fitzpatrick
, De Liang Long
, Stuart A. Macgregor
, Graeme Cooke^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	7220-7225
Number of pages	6
Journal	Dalton Transactions
Volume	45
Issue number	17
DOIs	https://doi.org/10.1039/c6dt00875e
Publication status	Published - 7 May 2016

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title = "Redox-mediated reactions of vinylferrocene: Toward redox auxiliaries",

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.",

author = "Wiles, \{Alan A.\} and Xiaolu Zhang and Brian Fitzpatrick and Long, \{De Liang\} and Macgregor, \{Stuart A.\} and Graeme Cooke",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

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doi = "10.1039/c6dt00875e",

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T1 - Redox-mediated reactions of vinylferrocene

T2 - Toward redox auxiliaries

AU - Wiles, Alan A.

AU - Zhang, Xiaolu

AU - Fitzpatrick, Brian

AU - Long, De Liang

AU - Macgregor, Stuart A.

AU - Cooke, Graeme

PY - 2016/5/7

Y1 - 2016/5/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84969247176

U2 - 10.1039/c6dt00875e

DO - 10.1039/c6dt00875e

M3 - Article

AN - SCOPUS:84969247176

SN - 1477-9226

VL - 45

SP - 7220

EP - 7225

JO - Dalton Transactions

JF - Dalton Transactions

IS - 17

ER -

Redox-mediated reactions of vinylferrocene: Toward redox auxiliaries

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