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Sulfur diimides are chemical compounds of the formula S(NR)2. 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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Organic derivatives
A particularly stable derivative is di-t-butylsulfurdiimide. A yellow oil, 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. Other routes to sulfur diimides involve treatment of sulfur tetrafluoride with amines. A third route involves transimidation of disulfonylsulfodiimide:
S(NSO2Ph)2 + 2 RNH2 → S(NR)2 + 2 PhSO2NH2Structure, bonding, reactions
These compounds are related to SO2. They have planar SN2C2 cores, although both syn and anti isomers are observed.
Sulfur diimides are electrophilic. They undergo Diels-Alder reaction with dienes. Organolithium compounds add to give the corresponding anions:
R'Li + S(NR)2 → R'S(NR)(NRLi)The triimido analogues of sulfite can be generated by treating the sulfur diimides with amide: