Synthesis and attempted reductions of bulky 1,3,5-triazapentadienyl groups 2 and 13 halide complexes

Indrek Pernik, Brant J. Maitland, Andreas Stasch, Cameron Jones

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Three extremely bulky 1,3,5-triazapentadienes, ArNNNH (ArNNN = N{C(But)=N(Ar)}2; Ar = Mes (mesityl), Dep (2,6-diethylphenyl), or Dip (2,6-diisopropylphenyl)) have been prepared and structurally characterized. These are readily deprotonated, yielding a series of lithium and potassium triazapentadienyl complexes, one of which, (DipNNN)Li, has been structurally characterized. Similarly, three monomeric triazapentadienyl magnesium iodide complexes, (ArNNN)MgI(OEt2), and a dimeric calcium counterpart, {(MesNNN)Ca(THF)(μ-I)}2, have been prepared. Attempts to reduce the former gave homoleptic bis(triazapentadienyl) magnesium complexes, (ArNNN)2Mg (Ar = Mes or Dep) as the main products. One reaction also gave a very low yield of the magnesium(I) dimer, {(DepNNN)Mg-}2, which was structurally characterized. In related chemistry, two triazapentadienyl boron difluoride compounds, (ArNNN)BF2 (Ar = Mes or Dep), have been synthesized, and unsuccessful attempts have been made to reduce these to boron(I) heterocycles. For sake of comparison, attempts have been made to prepare a series of related amino-substituted β-diketiminato group 13 element(I) heterocycles. Although these were also not successful, several group 13 element(III) halide complexes incorporating this ligand class have been characterized.

Original languageEnglish
Pages (from-to)513-521
Number of pages9
JournalCanadian Journal of Chemistry
Issue number6
Publication statusPublished - Jun 2018


  • Group 13
  • Group 2
  • Magnesium(I)
  • Steric bulk
  • Triazapentadienyl
  • β-diketiminate

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