Investigating the Ring Expansion Reaction of Pentaphenylborole and an Azide

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This article was originally published as:

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. Chemical Communications, 50(79), 11724-11726. doi:10.1039/C4CC04864D



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.


Used by permission: Royal Society of Chemistry

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At the time of writing David Wilson was affiliated with Avondale College as a Conjoint Lecturer.