Bis(trimethylsilyl)diimine: Preparation,Structure, and Reactivity

The highly reactive compound bis(trimethylsilyl)diimine (BSD), which was first prepared by oxidation of lithium tris(trimethylsilyl)hydrazide, is light blue, sensitive to thermolysis and hydrolysis, and ignites spontaneously in air. On the basis of electron transfer, acid-base, or free-radical reactions, it acts in particular as a (preparatively useful) redox system and as an agent for the introduction of azo groups. Redox reactions lead by oxidation or reduction of the other reactant through two oxidation stages to hydrazine derivatives or molecular nitrogen, and in the case of electrochemical reduction, to BSD radical-anions. Azo-group transfers, on the other hand, yield new inorganic azo compounds with no change in the oxidation state of the diimine group.