Benzenethiolato tributyltin

Submitted by PAUL M. TREICHEL and MARVIN H. TEGEN Checked by STEPHEN A. KOCHt 

Organotin thiolate complexes such as the title compound are useful reagents for the synthesis of transition metal complexes with RS ligands. Examples of this use are given in the procedures that follow this synthesis. 

It is possible to prepare compounds of the general formula Sn(SR )R3 from reactions of a mercaptan (R SH) and either Sn(hal)R3 (hal = Cl, Br, I), Sn(OH)R3, or (R3Sn)20 (R,R = alkyl, aryl groups).The example given here uses x-oxo-bis(tributyltin) as the organotin precursor because this is one of the least expensive tin compounds available. 

8 g (0.050 mol) sample of [(/i-C4H )3Sn]20 is placed in a 100 mL, three-neck, round-bottom flask equipped with magnetic stirrer, condenser, dropping funnel, and nitrogen inlet. From the dropping funnel, 11.0 mL (0.107 mol) of CsHsSH is added slowly. A reaction occurs immediately as 

It is reported that (R3Sn)20 compounds react with acids (HX) that have ionization costants between 10 and 10 ° to produce SnXR3 species. Thus, the preparation of Sn(SPh)(/i-C4H9)3 is an example of a more general synthetic procedure. 

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Benzenethiolato)tributyltin is a clear, viscous liquid. It is thermally stable and unreactive toward either oxygen or water under ambient conditions. This procedure can be used to prepare many other similar compounds including Sn(SCH3)(/i-C4H9)3 (bp 118-122°, 0.8 torr) and Sn[SC(CH3)3](n-C4H9)3 (bp 138-143°, 0.8 torr). 

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