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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Bibliographic Details
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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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805124