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Article Abstract
The solventless synthesis of tris(pyrazolyl)phenylmethane ligands of formula C₆H₅C(Pz)₃ (R = H, Me), starting from PhCCl₃ and 3,5-dimethylpyrazole (Pz) or pyrazole (Pz) was performed. The sterically crowded C₆H₅C(Pz)₃ is thermally transformed into the bis(pyrazolyl)(-pyrazolyl)phenylmethane ligand Pz-C₆H₄CH(Pz)₂. In this compound both Pz rings are linked through the N-atom to the methine C-atom. At higher temperatures, the binding mode of Pz changes from N1 to C4. All transformations occurred via quinonoid carbocation intermediates that undergo an aromatic electrophilic substitution on the 4-position of Pz. Reaction conditions were established to obtain five tris(pyrazolyl)phenylmethane ligands in moderate to good yields. ¹H- and C-NMR spectroscopy and X-ray diffraction of single crystals support the proposed structures.
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| http://dx.doi.org/10.3390/molecules22030441 | DOI Listing |
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