Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2024 Jan 11;30(3):e202303133.
doi: 10.1002/chem.202303133. Epub 2023 Nov 20.

9-Azahomocubane

Tyler Fahrenhorst-Jones  1 , David L Marshall  2 , Jed M Burns  1 , Gregory K Pierens  3 , Derek P Van Meurs  4 , Dehui Kong  1 , Paul V Bernhardt  1 , Stephen J Blanksby  2 , G Paul Savage  5 , Philip E Eaton  4 , Craig M Williams  1
Affiliations

9-Azahomocubane

Tyler Fahrenhorst-Jones et al. Chemistry. .

Abstract

Homocubane, a highly strained cage hydrocarbon, contains two very different positions for the introduction of a nitrogen atom into the skeleton, e. g., a position 1 exchange results in a tertiary amine whereas position 9 yields a secondary amine. Herein reported is the synthesis of 9-azahomocubane along with associated structural characterization, physical property analysis and chemical reactivity. Not only is 9-azahomocubane readily synthesized, and found to be stable as predicted, the basicity of the secondary amine was observed to be significantly lower than the structurally related azabicyclo[2.2.1]heptane, although similar to 1-azahomocubane.

Keywords: azahomocubane; cubane; homocubane; hydrocarbons; strained molecules.

PubMed Disclaimer

References

    1. T. Fahrenhorst-Jones, D. L. Marshall, J. M. Burns, G. K. Pierens, R. E. Hormann, A. M. Fisher, P. V. Bernhardt, S. J. Blanksby, G. P. Savage, P. E. Eaton, C. M. Williams, Chem. Sci. 2023, 14, 2821-2825.
    1. W. G. Dauben, D. L. Whalen, Tetrahedron Lett. 1966, 7, 3743-3750.
    1. G. L. Dunn, V. J. DiPasquo, J. R. E. Hoover, Tetrahedron Lett. 1966, 7, 3737-3742.
    1. P. E. Eaton, R. E. Hormann, J. Am. Chem. Soc. 1987, 109, 1268-1269.
    1. P. E. Eaton, A. M. Fisher, R. E. Hormann, Synlett 1990, 1990, 737-738.

LinkOut - more resources