Английская Википедия:Bis(trimethylsilyl)sulfide
Bis(trimethylsilyl) sulfide is the chemical compound with the formula ((CH3)3Si)2S. Often abbreviated (tms)2S, this colourless, vile-smelling liquid is a useful aprotic source of "S2−" in chemical synthesis.[1]
Synthesis
The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide:[2]
- 2 (CH3)3SiCl + Na2S → ((CH3)3Si)2S + 2 NaCl
((CH3)3Si)2S must be protected from air because it hydrolyzes readily:
- ((CH3)3Si)2S + H2O → ((CH3)3Si)2O + H2S
Use in synthesis
Bis(trimethylsilyl)sulfide is a reagent for the conversion of metal oxides and chlorides into the corresponding sulfides.[3] This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is:
- ((CH3)3Si)2S + MO → ((CH3)3Si)2O + MS
In a similar way, it has been used in the conversion of aldehydes and ketones to the corresponding thiones.[4][5]
Safety
((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.
References
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite book
- ↑ Lee, S. C.; Holm, R. H., "Nonmolecular Metal Chalcogenide/Halide Solids and Their Molecular Cluster Analogues", Angewandte Chemie International Edition in English, 1990, volume 29, pages 840-856.
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
