Organic Syntheses Utilizing Trimethylsilyldiazomethane

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Synthetic utilizations of trimethylsilyldiazomethane (TMSCHN_2), as a stable and safe substitute for hazardous diazomethane, were investigated as follows: 1. The cuprous chloride-catalyzed decomposition of alpha-trimethylsilyldiazoalkanes gives (E)-1-trimethylsilyl-1-alkenes in high yields. 2. Lithium trimethylsilyldiazomethane smoothly reacts with ketenimines to give 1,2,3-triazoles in good yields. 3. Most of the reactions of TMSCHN_2 with various olefins in the presence or absence of metal salt catalysts give silylcyclopropanes. 4. The rhodium(II) pivalate-catalyzed decomposition of alpha-trimethylsilyldiazoalkanes stereoselectively affords (Z)-1-trimethylsilyl-1-alkenes,in,good yields. 5. Reaction of TMSCHN_2 with various quinones affords indazoles, silylcyclopropanes, 2-substituted 3-trimethylsilylmethylml,4-quinones, and trimethylsilylmethylenedioxy derivatives,depending upon substrates.