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Molecules 2017, 22(3), 441; doi:10.3390/molecules22030441

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

1
Laboratorio de Química Supramolecular y Nanociencias, Instituto Politécnico Nacional-UPIBI, Av. Acueducto s/n Barrio la Laguna Ticomán, Ciudad de México C.P. 07340, Mexico
2
Facultad de Ciencias Químicas, Universidad de Colima, Km. 9 Carretera Colima-Coquimatlán, Coquimatlán C.P. 28400, Mexico
*
Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 8 February 2017 / Revised: 1 March 2017 / Accepted: 6 March 2017 / Published: 11 March 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

The solventless synthesis of tris(pyrazolyl)phenylmethane ligands of formula C6H5C(PzR2)3 (R = H, Me), starting from PhCCl3 and 3,5-dimethylpyrazole (PzMe2) or pyrazole (Pz) was performed. The sterically crowded C6H5C(PzMe2)3 is thermally transformed into the bis(pyrazolyl)(p-pyrazolyl)phenylmethane ligand PzMe2-C6H4CH(PzMe2)2. In this compound both PzMe2 rings are linked through the N-atom to the methine C-atom. At higher temperatures, the binding mode of PzMe2 changes from N1 to C4. All transformations occurred via quinonoid carbocation intermediates that undergo an aromatic electrophilic substitution on the 4-position of PzMe2. Reaction conditions were established to obtain five tris(pyrazolyl)phenylmethane ligands in moderate to good yields. 1H- and 13C-NMR spectroscopy and X-ray diffraction of single crystals support the proposed structures. View Full-Text
Keywords: thermal synthesis; tris(pyrazolyl)phenylmethane; bis(pyrazolyl)phenylmethane; poly(pyrazolyl)methane; three-bladed propeller; X-ray molecular structure thermal synthesis; tris(pyrazolyl)phenylmethane; bis(pyrazolyl)phenylmethane; poly(pyrazolyl)methane; three-bladed propeller; X-ray molecular structure
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Rodríguez-Venegas, E.; García-Báez, E.V.; Martínez-Martínez, F.J.; Cruz, A.; Padilla-Martínez, I.I. Solventless Synthesis of Poly(pyrazolyl)phenyl-methane Ligands and Thermal Transformation of Tris(3,5-dimethylpyrazol-1-yl)phenylmethane. Molecules 2017, 22, 441.

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