Oral Presentation Royal Australian Chemical Institute National Congress 2026

Exploring the reactivity of cubenes (138077)

Andy Wong 1 , Yannick J Esvan 2 , Sarah Livesley 2 , Susannah C Coote 1 , Christophe Aïssa 2
  1. Department of Chemistry, University of Bath, Bath, England, United Kingdom
  2. Department of Chemistry, University of Liverpool, Liverpool, England, United Kingdom

The release of geometric distortion1 has emerged as a powerful strategy for bond formation, whereby the generation of highly reactive strained intermediates enables access to complex molecules relevant to natural product synthesis and bio-orthogonal chemistry.

Cubene (1,2-dehydrocubane) is a strained, transient alkene that has been under-exploited in cubane chemistry, largely due to challenges in its preparation and inherent instability. Early efforts2,3 described elimination-based approaches to access cubene followed by its immediate trapping. Recent studies showed that cubene could engage in cycloaddition reactions with select trapping agents4, however, examples of the nucleophilic trapping of cubene are scarce in the literature. A broader investigation into cubene reactivity would be therefore instructive for the preparation of diverse cubane derivatives. Additionally, substituted cubenes are of particular interest as they have the potential to form regioisomeric products, yet their reactivity remains poorly understood.

This presentation will highlight our latest results in this area, demonstrating the synthetic potential of cubenes as reactive intermediates.

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  2. P. E. Eaton and Michele. Maggini, J. Am. Chem. Soc., 1988, 110, 7230–7232.
  3. K. Lukin and P. E. Eaton, J. Am. Chem. Soc., 1995, 117, 7652–7656.
  4. J. Ding, S. A. French, C. A. Rivera, A. Tena Meza, D. C. Witkowski, K. N. Houk and N. K. Garg, Nat. Chem., 2026, 1–10.