BEHAVIOR OF BU(CH2=CHCH2)SNCL2 IN WATER AND WATER-COSOLVENT MEDIA - AN APPROACH TO UNDERSTANDING THE CHEMICAL DEGRADATION OF ORGANOTINS IN AQUATIC ENVIRONMENTS

The behaviour of allylbutyltin dichloride in water, water-ethanol and water-hexane media, under either homogeneous or heterogeneous conditions, has been studied. 1,3-Diallyl-1,3-dibutyl-1,3-dichlorodistannoxane, butyltin di(hydroxy)chloride and butyltin trichloride arise from the solvolytic, acid-base and degradation processes. The degradation process involving the cleavage of the tin-carbon allyl bond has been interpreted to occur via an intramolecular reaction at the expense of the cation [Bu(CH2=CHCH2)Sn(OH)(H2O)(n)](+). The mechanistic pathway is ascribable to an internal interaction of the electrophilic cation with a bonded water molecule. This mechanistic proposal may be of some help with understanding of the chemical degradation of diorganotin derivatives in aquatic environments