Organometallic diazoalkanes. Part I. Synthesis and characterisation of simple group IVBorganometallic diazomethanes, and the tin–carbon cleavage reactions of bis(trimethylstannyl)diazomethane

Abstract

The synthesis and characterisation of the Group IVB organometallic diazomethanes is described. The compounds prepared were Me₃Si·CHN₂, (Me₃M)₂CN₂(M = Ge, Sn, or Pb), Me₃Si(Me₃Sn)CN₂, (Ph₃Ge)₂, and (R₃Sn)₂CN₂(R = Et, Buⁿ, or Ph). Two preparative methods have been explored: from diazomethane and the metal amide R₃M·NMe₂, and from diazomethyl-lithium and the appropriate chloride; their scope and limitation is discussed. The compounds are volatile, non-explosive, photosensitive, and reactive. Six Sn–C cleavage reactions of (Me₃Sn)₂CN₂ are described; nitrogen is generally lost and the carbene (Me₃Sn)₂C: may be an intermediate.