In this contribution, we present the reactions of two different three-dimensional analogues of 9,10-diyhdro-9,10-diboraanthracene (3D-DBAs), which act as dual-site Lewis superacids, with water. While 3D-DBACl (Cl on boron) readily reacts with water to yield the first hydroxy-functionalized 3D-DBA (3D-DBAOH), the phenyl derivative 3D-DBAPh forms a water adduct, 3D-DBAPh·(H2O)2, which is stable in THF and H2O and has been single crystal structurally characterized. All new compounds have been analyzed by NMR spectroscopy, single crystal X-ray diffraction analysis and elemental analysis. Quantum chemical calculations demonstrate the considerably high water affinity of 3D-DBAPh and the Brønsted superacidity of 3D-DBAOH and 3D-DBAPh·(H2O)2.
Bolch et al. (Thu,) studied this question.