Synthesis and Lewis Acidic Behavior of a Cationic 9-Thia-10-boraanthracene Academic Article uri icon

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 max = 392 nm which, as confirmed by computational studies, arises from a -* 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. 2010 American Chemical Society.

published proceedings

  • ORGANOMETALLICS

author list (cited authors)

  • Matsumoto, T., Wade, C. R., & Gabbai, F. P.

citation count

  • 40

complete list of authors

  • Matsumoto, Takeshi||Wade, Casey R||Gabbaii, Francois P

publication date

  • November 2010