96863-40-0Relevant academic research and scientific papers
THE ESR SPECTRA, STRUCTURE, AND REACTIVITY OF AROMATIC RADICAL-CATIONS IN SUPERACIDS
Rudenko, A. P.
, p. 1946 - 1980 (2007/10/03)
The oxidation of aromatic compounds by lead dioxide in superacids based on fluorosulfonic acid at -75 deg C takes place by a one-electron mechanism and leads in many cases to relatively stable radical-cations.The ESR spectra, the isotropic hyperfine coupling constants, data on the reactivity of the radical-cations, and the structures of the final products from their transformations under "long-life" conditions are presented.
OXIDATION OF METHYL-SUBSTITUTED BENZENESULFONYL FLUORIDES IN THE PbO2-HSO3F SYSTEM
Arapov, O. V.,Rudenko, A. P.,Zarubin, M. Ya.
, p. 152 - 163 (2007/10/02)
The transformations of the sulfonyl fluorides of methyl-substituted benzenes in the PbO2-HSO3F system were studied.They take place through a stage involving the one-electron oxidation of the substrate to aromatic radical-cations.One of the transformation paths of the latter is realized through the elimination of a proton from the methyl groups involved to the greatest degree in the delocalization of the unpaired electron.This leads to the formation of diarylmethanes and the fluorosulfonates of substituted benzyl alcohols, which give substituted tolylsultones and benzyl alcohols during hydrolysis of the acid solution and methyl ethers of benzyl alcohols during methanolysis.The other path, which arises during localization of the unpaired electron in the unsubstituted positions of the benzene ring, leads to biaryls.
