Organotin(IV) compounds are being used for many applications, e.g., as stabilizers in PVC, in anti-fouling paints and coatings for the protection of ship hulls and as precursors for SnO 2 -coatings on glass. Tetraorganotins and especially organotin(IV) halides often serve as synthetic precursors. A wide range of methods for the synthetic preparation of these compounds has been developed since the 1940s. This review gives an overview of the available routes for the preparation of organotin(IV) compounds and discusses their selectivity and yield. In particular, monoorganotin trihalides are often not accessible in high yield.
The Sn(IV) butyl complexes [Bu n SnCl 3 À n (NCN)] (NCN = [C 6 H 3 (CH 2 NMe 2 ) 2 -2,6] À , n = 1 (1), 2 (2), 3 (3)) were prepared. Spectroscopic analysis of 1-3 by 1 H and 119 Sn NMR gave evidence for the presence of intramolecular N ! Sn interactions in solution. The molecular structure of 1, as determined by a single-crystal X-ray diffraction study, revealed that it contained a six-coordinate Sn ( À or [SnCl 4 (aryl)] À stannate anion, respectively, with in each case one coordinated ortho-amine function and one protonated amine moiety involved in N-HÁ Á ÁCl-Sn hydrogen bonding in both compounds (2.14 Å for 6 and 2.18 Å for 8).
The Kocheshkov redistribution reaction of tetraalkyltin or dialkyltin dichlorides with tin tetrachloride is effectively catalysed by platinum(II) or palladium(II) phosphine complexes, yielding alkyltin trichlorides in high yield and with high selectivity.
Organotin(IV) compounds are being used for many applications, e.g., as stabilizers in PVC, in anti-fouling paints and coatings for the protection of ship hulls and as precursors for SnO 2 -coatings on glass. Tetraorganotins and especially organotin(IV) halides often serve as synthetic precursors. A wide range of methods for the synthetic preparation of these compounds has been developed since the 1940s. This review gives an overview of the available routes for the preparation of organotin(IV) compounds and discusses their selectivity and yield. In particular, monoorganotin trihalides are often not accessible in high yield.
Abstract-The reaction of 3-haloalkenes (3-chloropropene, 3-bromopropene, 3-chloro-2-methylpropene, 1-chloro-2-butene) with SnX 2 (X¼Cl, Br) to form mono-allyltin trihalides, was catalyzed by several platinum and palladium complexes of the type MZ 2 L (M¼Pt, Pd; Z¼Me, Cl; L¼2,2 0 -bipyridine, 1,10-phenanthroline or dppe). The highest yield of allyltin trichloride was obtained for the reaction of 3-chloropropene with SnCl 2 catalyzed by PdMe 2 (phen) (83%) while the yield obtained with the other catalysts decreased in the order PdCl 2 (phen), PdCl 2 (bipy).PdMe 2 (bipy).PtCl 2 (phen).PtMe 2 (bipy).PtMe 2 (phen).PtCl 2 (bipy). Interestingly, PdCl 2 (PhCN) 2 and Pd(PPh 3 ) 4 had no activity at all. The yield of allyltin trichloride was not only dependent on the activity of the catalyst but also on the decomposition rate of the product in the presence of the catalyst. 3-Bromopropene gave 19% of allyltin tribromide when reacted with SnBr 2 . The other 3-haloalkenes did react but the resulting monoallylictin trihalides were not stable enough to produce significant yields. Reaction of both, benzyl chloride and chlorobenzene, led to catalyst decomposition. In addition, SnCl 2 catalyzed formation of polybenzyl was observed in the case of benzyl chloride. q
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