29527-01-3Relevant academic research and scientific papers
Regiochemistry and mechanism of oxidation of N-benzyl-N-alkylhydroxylamines to nitrones
Hassan, Azfar,Wazeer, Mohammed I. M.,Saeed, Mohammed T.,Siddiqui, Mohammad N.,Ali, Sk. Asrof
, p. 443 - 451 (2007/10/03)
The oxidation of various N-(o-, m-, p-substituted benzyl)-N-alkylhydroxylamines and their dideuteriobenzyl (PhCD2) counterparts was carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. An overwhelming preference for the formation of conjugated nitrones is observed in the oxidation of N-benzyl-N-isopropylhydroxylamines. Considerable intra- and intermolecular kinetic isotope effects and negative ρ values in the Hammet plots point towards a mechanistic pathway that involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction. The conformation of unstable (E)-nitrones, which readily isomerize to the more stable (Z)-nitrones, is deduced from 1H NMR data. The E ? Z isomerization was found to be a bimolecular process. Copyright
DYNAMIC STEREOCHEMISTRY OF IMINES AND DERIVATIVES. PART 18. PHOTOSYNTHESIS AND PHOTORACEMIZATION OF OPTICALLY ACTIVE OXAZIRIDINES
Boyd, Derek R.,Campbell, Rose M.,Coulter, Peter B.,Grimshaw, James,Neill, David C.,Jennings, W. Brian
, p. 849 - 856 (2007/10/02)
Optically active oxaziridines have been synthesized with a maximum optical yield of 31percent by photoisomerization (λ > 300 nm) of achiral aldo- and keto-nitrones in the presence of the chiral solvent (+)-(S) or (-)-(R)-2,2,2-trifluoro-1-phenylethanol.Ph
