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2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties

Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, Academician Lavrentiev Ave. 9, Novosibirsk 630090, Russia
Institute of Chemical Kinetics & Combustion SB RAS, Institutskaya 3, Novosibirsk 630090, Russia
Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090, Russia
Authors to whom correspondence should be addressed.
Academic Editor: Francesca Marini
Molecules 2020, 25(4), 845; (registering DOI)
Received: 31 January 2020 / Accepted: 13 February 2020 / Published: 14 February 2020
(This article belongs to the Special Issue Stable radicals: synthesis, structure and applications)
Nitroxides are broadly used as molecular probes and labels in biophysics, structural biology, and biomedical research. Resistance of a nitroxide group bearing an unpaired electron to chemical reduction with low-molecular-weight antioxidants and enzymatic systems is of critical importance for these applications. The redox properties of nitroxides are known to depend on the ring size (for cyclic nitroxides) and electronic and steric effects of the substituents. Here, two highly strained nitroxides, 5-(tert-butyl)-5-butyl-2,2-diethyl-3-hydroxypyrrolidin-1-oxyl (4) and 2-(tert-butyl)-2-butyl-5,5-diethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl (5), were prepared via a reaction of the corresponding 2-tert-butyl-1-pyrroline 1-oxides with butyllithium. Thermal stability and kinetics of reduction of the new nitroxides by ascorbic acid were studied. Nitroxide 5 showed the highest resistance to reduction.
Keywords: nitroxides; nitrones; 1,3-dipolar cycloaddition reaction; organolithium compounds; EPR; spin probes; reduction kinetics nitroxides; nitrones; 1,3-dipolar cycloaddition reaction; organolithium compounds; EPR; spin probes; reduction kinetics
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Zhurko, I.F.; Dobrynin, S.; Gorodetskii, A.A.; Glazachev, Y.I.; Rybalova, T.V.; Chernyak, E.I.; Asanbaeva, N.; Bagryanskaya, E.G.; Kirilyuk, I.A. 2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties. Molecules 2020, 25, 845.

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