Английская Википедия:Bis(trimethylsilyl)sulfide

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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]

Файл:ASUTAJ = CCDB code. Ag-S nanocrystal as described in doi 10.1002SLASHanie.200352351.png
Large Ag-S cluster prepared with the use of bis(trimethylsilyl)sulfide.[6]

Safety

((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.

References

Шаблон:Reflist

  1. Шаблон:Cite journal
  2. Шаблон:Cite book
  3. 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.
  4. Шаблон:Cite journal
  5. Шаблон:Cite journal
  6. Шаблон:Cite journal