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.
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IUPAC name
diimino-λ4-sulfane
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Other names
2λ4-Diazathia-1,2-diene
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3D model (JSmol)
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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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A particularly stable derivative is di-t-butylsulfurdiimide.[1] 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. A second route to sulfur diimides involve treatment of sulfur tetrafluoride with amines. A third route involves transimidation of disulfonylsulfodiimide:
N,N'-Bis(methoxycarbonyl)sulfur diimide (MeO2C-N=S=N-CO2Me) is obtained from methyl carbamate.[2]
These compounds are related to SO2. They have planar C–N=S=N–C cores with bent C–N=S and N=S=N geometries, and various combinations of E and Z isomers are observed for the two N=S bonds.[3]
Sulfur diimides are electrophilic. They undergo Diels–Alder reactions with dienes.[1] Organolithium reagents attack at the sulfur to give the corresponding nitrogen anion:
The triimido analogues of sulfite can be generated by treating the sulfur diimides with a metal amide:[4]