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The solventless synthesis of tris(pyrazolyl)phenylmethane ligands of formula C₆H₅C(Pz R2 )₃ (R = H, Me), starting from PhCCl₃ and 3,5-dimethylpyrazole (Pz Me2 ) or pyrazole (Pz) was performed. The sterically crowded C₆H₅C(Pz Me2 )₃ is thermally transformed into the bis(pyrazolyl)( p -pyrazolyl)phenylmethane ligand Pz Me2 -C₆H₄CH(Pz Me2 )₂. In this compound both Pz Me2 rings are linked through the N-atom to the methine C-atom. At higher temperatures, the binding mode of Pz Me2 changes from N1 to C4. All transformations occurred via quinonoid carbocation intermediates that undergo an aromatic electrophilic substitution on the 4-position of Pz Me2 . Reaction conditions were established to obtain five tris(pyrazolyl)phenylmethane ligands in moderate to good yields. ¹H- and 13 C-NMR spectroscopy and X-ray diffraction of single crystals support the proposed structures.

Solventless Synthesis of Poly(pyrazolyl)phenyl-methane Ligands and Thermal Transformation of Tris(3,5-dimethylpyrazol-1-yl)phenylmethane