Acta Cryst. (2001). E57, o985-o987  [ doi:10.1107/S160053680101563X ]

3-(2-Bromophenyl)-4-(triisopropylsilyl)sydnone

D. A. Grossie, K. Turnbull and D. M. Krein

Abstract: Sydnones are, in most cases, extremely stable crystalline compounds that exhibit a distinct polarity. The five-membered heterocyclic ring that characterizes a sydnone is subject to electrophilic substitution. Only with a strongly activating group present will an attached aryl group compete effectively for the electrophile, due to the considerable partial positive change at the quaternary N atom of the sydnone ring. The title compound, C₁₇H₂₅BrN₂O₂Si, is of interest due to an intramolecular shift of the silyl-protecting group that occurs between the syndone ring and the aryl ring when treated with n-butyllithium. This was observed while attempting to replace the aryl bromine. With a curiosity into a rationale for this shift, we have examined a series of precursors, this being the first.

Online 29 September 2001

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