Issue 11, 2023



Highly strained cage hydrocarbons have long stood as fundamental molecules to explore the limits of chemical stability and reactivity, probe physical properties, and more recently as bioactive molecules and in materials discovery. Interestingly, the nitrogenous congeners have attracted much less attention. Previously absent from the literature, azahomocubanes, offer an opportunity to investigate the effects of a nitrogen atom when incorporated into a highly constrained polycyclic environment. Herein disclosed is the synthesis of 1-azahomocubane, accompanied by comprehensive structural characterization, physical property analysis and chemical reactivity. These data support the conclusion that nitrogen is remarkably well tolerated in a highly strained environment.

Graphical abstract: 1-Azahomocubane

Supplementary files

Article information

Article type
Edge Article
01 Jan 2023
02 Feb 2023
First published
22 Feb 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 2821-2825


T. Fahrenhorst-Jones, David L. Marshall, Jed. M. Burns, G. K. Pierens, R. E. Hormann, A. M. Fisher, P. V. Bernhardt, S. J. Blanksby, G. P. Savage, P. E. Eaton and C. M. Williams, Chem. Sci., 2023, 14, 2821 DOI: 10.1039/D3SC00001J

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