67765-80-4Relevant academic research and scientific papers
Free radicals trapping reactions with 3,5-di-t-butyl-nitrosobenzene. The Α-nitrobenzyl free radical
Badea, Florin,Iordache, Florin,Costea, Ion,Iordache, ?tefan,Meghea, Aurelia,Simion, Alina,Simion, Cristian
, p. 361 - 368 (2007/10/03)
The reactions of sodium and potassium phenylnitrolates (the salts of aci-phenylnitromethane) with iodine, studied by Nenitzescu in 1929,1 were reinvestigated in order to detect the α-nitrobenzyl free radical. In agreement with Nenitzescu we confirmed that only (±)-α,α′-dinitrodibenzyl (m.p. 150°) resulted on treating the salts with iodine at 0-5°. The meso modification (m.p. 236-237°) does not seem to be formed in any reaction conditions used either by Nenitzescu or by us in this work. Addition of an iodine crystal to a suspension of sodium phenylnitrolate in dry benzene and immediate recording of the ESR spectrum allowed the observation of a nitrogen free radical (aN = 0.458 mT; g = 2.0058), not agreeing with the structure of the simple α-nitrobenzyl free radical. Dry potassium pbenylnitrolate kept in a dry air atmosphere is transformed in 3,4,5-triphenylisoxazole. Possible structures for the observed radical and the pathway leading to its formation are discussed in relation to trans-stilbene formation.
Addition Reactions of Cation Radicals of Nitroalkanes to Olefinic Compounds by the Use of Manganese(III) Pyridinecarboxylate
Narasaka, Koichi,Iwakura, Kazunori,Okauchi, Tatsuo
, p. 423 - 426 (2007/10/02)
Silyl derivatives of aci-nitroalkanes react with olefins such as silyl enol ether, vinyl sulfide, and enamine by oxidation with manganese(III) 2-pyridinecarboxylate to give the intermolecular addition products selectively.
Radical and Ionic Reactions of (Benzoylmethyl)mercurials
Russell, Glen A.,Kulkarni, Shekhar V.,Khanna, Rajive K.
, p. 1080 - 1086 (2007/10/02)
Photolysis of PhCOCH2HgCl or (PhCOCH2)2Hg yields benzoylmethyl radicals which can be trapped by anions such as Me2C=NO2-, RC(CO2Et)2-, RC(O-)=CH2 or by other electron-rich systems such as (RO)3P, N-methylpyrrole, enamines, or norbornene.Electron transfer from the adduct radicals to the mercurials yields PhCOCH2A from the anions A-, PhCOCH2P(O)(OR)2 from P(OR)3, and the phenacyl derivative from N-methylpyrrole or enamines.Easily oxidized anions such as PhCOCPh2- or PhC(CH3)=NO2- react with PhCOCH2* by electron transfer to yield the dimer derived from the anion.Addition of PhCOCH2* to norbornene yields a substituted 3-benzoylpropyl radical which cyclizes at the ortho position of the benzoyl group to give the α-tetralone derivative.
