Title

Investigating the Ring Expansion Reaction of Pentaphenylborole and an Azide

Document Type

Article

Publication Date

10-2014

Publication Details

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

ISSN:1364-548X

Abstract

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.

Comments

Used by permission: Royal Society of Chemistry

This article may be accessed from the publisher here.

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