Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations

The scope and limitations of Eaton's rhodium(I)‐catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigated in the context of functional group tolerability, multiple substitution modes and the ability of cubane‐alcohols to undergo one‐pot tandem Ley–Griffith Wittig re...

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Published in:Chemistry : a European journal 2019-02, Vol.25 (11), p.2735-2739
Main Authors: Houston, Sevan D., Xing, Hui, Bernhardt, Paul V., Vanden Berg, Timothy J., Tsanaktsidis, John, Savage, G. Paul, Williams, Craig M.
Format: Article
Language:English
Subjects:
Alcohols
Cascade chemical reactions
Chemistry
Cubane
cubanes
cyclooctatetraenes
Functional groups
Isomerization
Rhodium
tandem
Transition metals
valence isomerization
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cited_by cdi_FETCH-LOGICAL-c4394-f2a3a358a6929691336a628415d74309287b5e9670ecd23ad4ec62c20520862a3
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container_end_page 2739
container_issue 11
container_start_page 2735
container_title Chemistry : a European journal
container_volume 25
creator Houston, Sevan D.
Xing, Hui
Bernhardt, Paul V.
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Savage, G. Paul
Williams, Craig M.
description The scope and limitations of Eaton's rhodium(I)‐catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigated in the context of functional group tolerability, multiple substitution modes and the ability of cubane‐alcohols to undergo one‐pot tandem Ley–Griffith Wittig reactions in the absence of a transition metal catalyst. Releasing the strain! This work aims to take Eaton's rhodium(I)‐catalyzed valence isomerization of cubane to cyclooctatetraene (COT) to the next level. Functional group tolerability, scope, and limitations of this reaction were investigated in the context of developing deployable methodology for the increasing number of applications involving the COT ring system.
doi_str_mv 10.1002/chem.201805124
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source Wiley-Blackwell Read & Publish Collection
subjects Alcohols
Cascade chemical reactions
Chemistry
Cubane
cubanes
cyclooctatetraenes
Functional groups
Isomerization
Rhodium
tandem
Transition metals
valence isomerization
title Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations
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