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Behaviour of Bu(CH 2 —CHCH 2 )SnCl 2 in water and water‐cosolvent media: An approach to understanding the chemical degradation of organotins in aquatic environments
Author(s) -
Marton Daniele,
Stivanello Diego,
Tagliavini Giuseppe
Publication year - 1995
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590090717
Subject(s) - chemistry , degradation (telecommunications) , electrophile , chloride , intramolecular force , molecule , tin , organic chemistry , medicinal chemistry , catalysis , telecommunications , computer science
Abstract 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(CH 2 =CHCH 2 )Sn(OH)(H 2 O) 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.