18796-01-5Relevant academic research and scientific papers
Ammonium acetate as a catalyst of the condensation of sterically hindered functionalized hydroxylamines with ketones
Reznikov,Volodarsky
, p. 1577 - 1581 (1997)
Ammonium acetate was found to be a catalyst of the condensation of α-hydroxylamino oximes and α-hydroxylamino alcohols with ketones. This condensation leads to sterically hindered heterocyclic hydroxylamines, which are precursors of stable nitroxides.
Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds
Vasilevsky, Sergei F.,Krivenko, Olga L.,Alabugin, Igor V.
, p. 8246 - 8249 (2007)
In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI-PPh3-K2CO3-DMF catal
Synthetic and mechanistic aspects of cross-coupling of nitroxyl radicals of 3-imidazoline series with terminal alkynes
Vasilevsky, Sergei F.,Krivenko, Olga L.,Gorelik, Vitalii R.,Alabugin, Igor V.
, p. 8807 - 8814 (2008/12/21)
Practical synthetic approaches to the new class of acetylenic derivatives of 3-imidazolyl-3-oxide-1-oxyls, including biradicals, were developed through cross-coupling reactions of 3-imidazolyl halides with either terminal alkynes or their copper salts. The presence of nitroxyl functional group as an internal oxidant leads to a competition between the formation of cross-coupling products and the products of oxidative homocoupling. The balance in this competition can be shifted toward the cross-coupling products through the combination of factors that includes nature of the catalyst, reactivity of the halides, and reaction conditions.
Reduction of a nitroxide spin label by native and partially oxidized human low-density lipoprotein
Witting, Paul K.,Stocker, Roland
, p. 100 - 106 (2007/10/03)
The reduction of nitroxide compounds in vivo has in most part been assigned to the reaction with reductants such as ascorbic acid, reduced thiols and quinols such as ubiquinol or by reaction with simple carbon-centred radicals. In this study a water-solub
EFFECT OF THE CHEMICAL STRUCTURE OF NITROXYL RADICALS ON THEIR REACTIVITY IN THE REACTION WITH HYDRAZOBENZENE AND TETRANITROMETHANE
Malievskii, A. D.,Koroteev, S. V.,Volodarskii, L. B.,Shapiro, A. B.
, p. 2331 - 2338 (2007/10/02)
The reaction rate constants of reduction of stable radicals of different classes by hydrazobenzene in hexane at ca. 20 deg C, in the range of 0.4 - 5*103 M-1 sec-1, were determined; a single scale of the oxidative properties of stable nitroxyl radicals was constructed.The rate constants of oxidation of a series of nitroxyl radicals by tetranitromethane in aqueous medium at ca. 20 deg C, in the range of 0.06 - 10 M-1 sec-1, were determined.It was shown that the oxidative properties of the nitroxyl group decrease slightly with an increase in its reducing properties for nitroxyl radicals of the piperidine and imidazoline series in reactions with ascorbic acid and tetranitromethane in aqueous medium, respectively.
The Oxidative Properties of Nitroxy-radicals in Their Reactions with Sterically Hindered Hydroxylamines
Dikanov, S. A.,Grigor'ev, I. A.,Volodarskii, L. B.,Tsvetkov, Yu. D.
, p. 1696 - 1699 (2007/10/02)
A relative scale of the oxidative properties of cyclic nitroxy-radicals has been constructed and the influence of various structural factors on the oxidising capacity of the nitroxy-group in the radicals has been investigated.It is shown that the oxidative properties of the nitroxy-group in cyclic nitroxy-radicals become more pronounced with the increase in ring size.A relation has been established between the oxidative properties and the electron-accepting properties of functional groups separated from the nitroxy-group by two and more ?-bonds.
