Sulfur diimide
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
diimino-λ4-sulfane | |
| Other names
2λ4-Diazathia-1,2-diene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| Properties | |
| H2N2S | |
| Molar mass | 62.09 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sulfur diimides are chemical compounds of the formula S(NR)2. Structurally, they are the diimine of sulfur dioxide. The parent member, S(NH)2, is of only theoretical interest. Other derivatives where R is an organic group are stable and useful reagents.
A particularly stable derivative is di-t-butylsulfurdiimide.[1][failed verification] It is prepared by reaction of tert-butylamine with sulfur dichloride to give the intermediate "S(N-t-Bu)", which decomposes at 60 °C to give the diimide.[citation needed] Contrariwise, the trimethylsilyl derivative S(NSiMe3)2 is prepared from lithium hexamethyldisilazane and thionyl chloride.[2]
However, most sulfur diimides are not produced from such elimination reactions. Typically, sulfur diimides arise from treatment of sulfur tetrafluoride with amines, or from transamidation reactions. The latter typically requires amide reactants that are less basic than the products,[3] as with disulfonylsulfodiimide...
- S(NSO2Ph)2 + 2 RNH2 → S(NR)2 + 2 PhSO2NH2
...or with N,N'-Bis(methoxycarbonyl)sulfur diimide (MeO2C-N=S=N-CO2Me) from methyl carbamate.[4] Alternatively, the presence of a strong base to absorb the released SO2 can drive transamidation from sulfinylamines.[3]