Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations

Sevan D Houston; Hui Xing; Paul V Bernhardt; Timothy J Vanden Berg; John Tsanaktsidis; G Paul Savage; Craig M Williams

doi:10.1002/chem.201805124

Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations

Chemistry. 2019 Feb 21;25(11):2735-2739. doi: 10.1002/chem.201805124. Epub 2019 Jan 29.

Authors

Sevan D Houston¹, Hui Xing¹, Paul V Bernhardt¹, Timothy J Vanden Berg¹, John Tsanaktsidis², G Paul Savage², Craig M Williams¹

Affiliations

¹ School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia.
² CSIRO Manufacturing, Ian Wark Laboratory, Melbourne, 3168, Victoria, Australia.

PMID: 30693963
DOI: 10.1002/chem.201805124

Abstract

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.

Keywords: cubanes; cyclooctatetraenes; rhodium; tandem; valence isomerization.

Grants and funding

Australian Research Council