Borazine dearomatization 2026-10-20
Borazine dearomatization interrupts the planar pi system, for example when a nucleophile makes one boron tetrahedral. In a metal pi complex, this can change ring hapticity and produce a charged ligand with a different donor count.
Past exam of the chemistry B course of the University of Cambridge 2024 Paper 2 B9 b i Solution 2026-10-20
The methyl nucleophile attacks an electrophilic ring boron. That boron becomes tetrahedral, bearing its original methyl, the incoming methyl, and its two ring nitrogen neighbors. This interrupts its p-orbital participation, so the metal attaches to the remaining five-atom conjugated segment. is the anionic heptamethylated-ring Cr(CO) complex, paired formally with ; solvent ligation and ion pairing at magnesium are not specified by the spectrum. The original connectivity, with the attacked boron labeled , is shown in the first panel below.
There are seven methyl groups. The two attached to tetrahedral are inequivalent because the chromium-bound face distinguishes their environments: one signal of relative integral one for each. The other two B–Me groups are equivalent to one another, giving a signal of integral two. The two N–Me groups adjacent to form another equivalent pair, while the N–Me opposite is unique. The predicted methyl-group multiplicities are therefore , the same unordered set as the observed ratio. Multiplying by three gives proton integrals totaling 21. This assignment assumes no fast process interchanging the two methyl environments.
