Martin, Caleb D.Dutton, Jason L.Wilson, David J.Thompson, Trevor K.Couchman, Shannon A.2023-11-012023-11-012014-10-112015-03-29<p>Couchman, S. A., Thompson, T. K., Wilson, D. J., Dutton, J. L., & Martin, C. D. (2014). Investigating the ring expansion reaction of pentaphenylborole and an azide. <em>Chemical Communications, 50</em>(79), 11724-11726. doi:10.1039/C4CC04864D</p>1359-7345https://doi.org/10.1039/C4CC04864Dhttps://research.avondale.edu.au/handle/123456789/06916447<p>The reaction between trimethylsilyl azide and pentaphenylborole was recently shown to produce the corresponding 1,2-azaborine. Investigating this transformation theoretically suggests that the reaction proceeds via coordination of the azide to the borole, rearrangement to a bicyclic species, and conversion to a kinetically favoured eightmembered BN3C4 heterocycle or expulsion of N2 to furnish the thermodynamically favoured 1,2-azaborine. The eight-membered species was structurally characterized as a borole adduct and represents an unusual analogue of cyclooctatetraene.</p>en-us<p>Due to copyright restrictions this article is unavailable for download.</p> <p>Published by the <a href="http://www.rsc.org/">Royal Society of Chemistry</a></p>reactionpentaphenylboroleJournal Article