5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants 3. Synthesis and antioxidant activity of 2-dodecylthiomethyland 2-dodecylselenomethyl-5-hydroxy-4,6,7-trimethyl-2,3-dihydrobenzofurans
- Authors: Yagunov S.E.1, Kholshin S.V.1, Kandalintseva N.V.1,2, Prosenko A.E.1,2
- 
							Affiliations: 
							- Novosibirsk State Pedagogical University
- Novosibirsk Research Institute of Antioxidant
 
- Issue: Vol 67, No 8 (2018)
- Pages: 1452-1458
- Section: Article
- URL: https://journals.rcsi.science/1066-5285/article/view/242823
- DOI: https://doi.org/10.1007/s11172-018-2239-8
- ID: 242823
Cite item
Abstract
New sulfur- and selenium-containing analogs of α-tocopherol, namely, 2-dodecylthiomethyl- and 2-dodecylselenomethyl-5-hydroxy-4,6,7-trimethyl-2,3-dihydrobenzofurans were synthesized from 4-ethoxy-3,5-dimethylphenol through intermediate 2-allyl-4-ethoxy-3,5,6- trimethylphenol, 2-iodomethyl-, 2-dodecylthiomethyl-, and 2-dodecylselenomethyl-5-ethoxy- 4,6,7-trimethyl-2,3-dihydrobenzofurans. The compounds terminated oxidation chains of AIBN-initiated oxidation of styrene at 50 °C with rate constant of 5.0•106 mol L–1 s–1 and stoichiometric coefficients of 1.9±0.1. The O—H bond dissociation energies for obtained compounds (326.5 kJ mol–1) are calculated based on the measured rate constants.
About the authors
S. E. Yagunov
Novosibirsk State Pedagogical University
							Author for correspondence.
							Email: syagunov@yandex.ru
				                					                																			                												                	Russian Federation, 							28 ul. Vilyuiskaya, Novosibirsk, 630126						
S. V. Kholshin
Novosibirsk State Pedagogical University
														Email: syagunov@yandex.ru
				                					                																			                												                	Russian Federation, 							28 ul. Vilyuiskaya, Novosibirsk, 630126						
N. V. Kandalintseva
Novosibirsk State Pedagogical University; Novosibirsk Research Institute of Antioxidant
														Email: syagunov@yandex.ru
				                					                																			                												                	Russian Federation, 							28 ul. Vilyuiskaya, Novosibirsk, 630126; 54a Krasnyi prosp., Novosibirsk, 630091						
A. E. Prosenko
Novosibirsk State Pedagogical University; Novosibirsk Research Institute of Antioxidant
														Email: syagunov@yandex.ru
				                					                																			                												                	Russian Federation, 							28 ul. Vilyuiskaya, Novosibirsk, 630126; 54a Krasnyi prosp., Novosibirsk, 630091						
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