Reversible adduct formation between phosphines and triarylboron compounds

Abstract

The acceptor strength of a number of Lewis-acidic fluorinated triarylboron compounds has been established and shown to depend on the amount and position of fluorine substitution. The donor strength of tert-butyl-phosphine has been found to be greater than phosphine towards these acceptor compounds; two series of adducts have been characterised and reversible adduct formation has been demonstrated for some adducts. Crystal structures of the phosphine adducts of tris(pentafluorophenyl)boron and tris(2,6-difluorophenyl)boron have been compared with those of the tert-butylphosphine adducts of tris(pentafluorophenyl)boron and tris(3,4,5-trifluorophenyl)boron to show a correlation between the length and the strength of the adduct bond. Mixing aryl groups in the acceptor compounds has not produced new adducts. The strong acceptor compounds have been found to form unstable adducts with water which act as drying agents ultimately producing arylboric acids; the crystal structure of (2,6-difluoropheny)dihydroxyborane has been determined.