THE INTERACTION OF BENZYL ALCOHOL WITH TRIMETHOXYBOROXINE - AMINE ADDUCTS OF TRIARYLBOROXINES AS MODEL COMPOUNDS

The interaction of benzyl alcohol with trimethoxyboroxine has been inv estigated by hydrogen-1 and carbon-13 NMR and IR spectroscopy. These t echniques indicate formation of a weak Lewis acid/base adduct, additio nally stabilized by a hydrogen-bonding interaction, which undergoes ra pid ligand exchange at room temperature. The system has been modelled by the synthesis and characterization of a series of amine-triarylboro xine adducts. These adducts rapidly undergo ligand dissociation-recomb ination in solution with Delta G(+) of ca. 40-50 kJ/mol.