ON THE CHARACTERIZATION OF THE REACTION OF ORGANOTIN COMPOUNDS WITH D-GLUCURONIC ACID

C-13 NMR spectroscopy and mass spectrometry show that D-glucuronic acid forms trialkyltin glucuronate complexes upon reaction with bis(tributyltin) oxide but not with tributyltin or trimethyltin chlorides in Me2SO or the trimethyltin chloride in water. Analysis of the C-13 NMR chemical shifts of the tributyltin D-glucuronate formed indicates that appreciable interaction of the d-orbitals on tin occurs with primarily the O-4 hydroxyl group and to a lesser extent with ring oxygen at C-1. Previous incorrect assignments of the C-13 NMR signals for D-glucuronic acid are discussed.