TRIMETHYLSILYLDIAZOMETHANE - A NEW SILICON REAGENT IN ORGANIC-SYNTHESIS

Various aspects of trimethylsilyldiazomethane (Me3SiCHN2, TMSCHN2) and its lithium salts (Me3SiC(Li)N2, TMSC(Li)N2) in organic synthesis as a stable and safe substitute for hazardous diazomethane are reviewed on the following items: 1) properties, 2) preparation, 3) application as a C1-unit introducing reagent, 4) application of [C-N-N] synthon for the preparation of azoles. As a C1-unit introducing reagent, TMSCHN2 and its lithium salt mostly behave in the same way as diazomethane. As a [C-N-N] azole synthon, however, they generally behave in an analogous but not the same way as diazomethane.