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A study of the disproportionation equilibrium for allyldibutyltin(IV) chloride as an approach to understanding the role of organotins in the aquatic environment
Author(s) -
Marton Daniele,
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.590090709
Subject(s) - chemistry , disproportionation , electrophile , nucleophile , medicinal chemistry , halogen , chloride , redistribution (election) , acetone , ionic liquid , stereochemistry , ionic bonding , organic chemistry , ion , alkyl , catalysis , politics , political science , law
The equilibrium: 2 Bu 2 (CH 2 =CHCH 2 )SnCl⇌Bu 2 Sn(CH 2 =CHCH 2 ) 2 + Bu 2 SnCl 2 takes place when the allyltin chloride is stirred in water. This has been chosen as a model to understand the extent as well as the mechanistic pattways of the disproportionation reactions 2 R 3 SnX⇌R 4 Sn + R 2 SnX 2 which are thought to occur in the aquatic environment. The behaviour of Bu 2 (CH 2 =CHCH 2 )SnCl has been studied in various media: water, water‐acetone, water‐ethanol and water‐hexane. It has also been ascertained that Bu 2 (CH 2 =CHCH 2 )SnCI is a product arising at room temperature from the scrambling of Bu 2 Sn(CH 2 ==CHCH 2 ) 2 and Bu 2 SnCI 2 either neat, in organic solvents or also in the presence of water. Equilibrium [1] has been interpreted as arising from a bimolecular interaction between the electrophilic aquo‐cation [Bu 2 (CH 2 =CHCH 2 )Sn(H 2 O) n ] + and the nucleophilic molecule Bu 2 (CH 2 =CHCH 2 )SnCl. Kinetic studies on R 3 SnMe/Me 2 SnX 2 (X = Cl, NO 3 ) systems in alcoholic solvents (R = Me, Et, n‐Pr, i‐Pr, n‐Bu) support the assumption that, in dissociating media, redistribution processes can be promoted by ionic electrophilic species.