Organometallic diazoalkanes. Part I. Synthesis and characterisation of simple group IVB organometallic 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.