Abstract
As part of our efforts in the chemistry of Lewis acidic organoboron compounds, we have synthesized a cationic borane ([1]+) featuring a 9-thia-10-boraanthracene moiety substituted at boron by the cationic anilium group [4-(Me3N)-2,6-Me2-C6H2]+. This new cationic borane has been fully characterized. Its UV−vis spectrum features a low-energy band at λmax = 392 nm which, as confirmed by computational studies, arises from a π−π* transition of the 9-thia-10-boraanthracene chromophore. As a result of the low steric bulk present around the boron center and the inductive effects imparted by the anilium group, [1]+ possesses unusual Lewis acidic properties and reacts with DMAP to form the corresponding adduct. This derivative also binds both fluoride and cyanide anions in THF to afford 1-F and 1-CN whose stability constants exceed 107 M−1. Although [1]+ is unstable in pure water, it can be used to selectively extract cyanide under biphasic conditions in nitromethane/water.
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