Lithium (trimethylsilyl)diazomethane

Lithium (trimethylsilyl)diazomethane 化学特性,用途語,生産方法

• 使用

  When generated in pentane/THF at ?100°C, diazo(trimethylsilyl)methyllithium reacts with ketones (three examples) and benzaldehyde to give the unstable 1-diazo-1-trimethylsilyl-2-alkanols (eq 2).On gentle warming, the diazo alcohols rapidly lose N2 to give trimethylsilyl epoxides. Since such epoxides readily give aldehydes on treatment with acid, the method represents an overall homologation of a ketone to the next higher aldehyde.
  When diaryl ketones are used, diarylalkynes are formed in good yield (eq 3).The reaction presumably proceeds via the diazoalkene followed by aryl migration with loss of nitrogen.

• 製造方法

  prepared in situ by lithiation of trimethylsilyldiazomethane using n-butyllithium; prepared in situ by lithiation of trimethylsilyldiazomethane (TMSCHN2) using butyllithium, lithium diisopopylamide (LDA), or lithium 2,2,6,6-tetramethylpiperidide (LTMP). The lithium salt is easily converted to the corresponding magnesium bromide salt (eq 1).

  

Lithium (trimethylsilyl)diazomethane 上流と下流の製品情報