Pyrazole-Containing o-Benzoquinones: Synthesis and Inhibitory Activity in Free-Radical Polymerization

• Published in: Russian journal of general chemistry 2023-12, Vol.93 (Suppl 3), p.S639-S648
• Main Authors: Shushunova, N. Yu, Khramova, D. V., Kovylina, T. A., Arsenyev, M. V., Zhiganshina, E. R., Chesnokov, S. A.
• Format: Article
• Language: English
• Subjects: Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Electrochemical analysis; Free radical polymerization; Methyl methacrylate; NMR spectroscopy; Nuclear magnetic resonance spectroscopy; Parameters; Polymerization; Polymethyl methacrylate; Pyrazole; Quinone; Quinones
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363223160028

A series of trisubstituted o -benzoquinones containing a (3,5-dimethyl-1 H -pyrazol-1-yl)methyl substituent at position 3 and two alkyl groups ( i -Pr, c -Hex, t -Bu, Ad) at positions 4 and 6 were synthesized. Their structures were confirmed by IR, 1 H, 13 C NMR spectroscopy methods. The electrochemical properties of the o -quinones were investigated by cyclic voltammetry method. The radical polymerization of methyl methacrylate at 60°C in the presence o -quinone (0.62–2.48 mM) was studied. The inhibitory ability of new quinone decreases ( i -Pr > c -Hex > t -Bu > Ad) with increasing of the Charton steric parameters of alkyl groups. The photoinitiating ability of the investigated quinones in pair with DMCHA were studied on the photocuring of OCM-2 by the LED@white (9.1 kLx). The photoinitiating ability of new quinone increase ( i -Pr < c -Hex < t -Bu < Ad) with increasing of the Charton steric parameters of alkyl groups.