10551-32-3Relevant articles and documents
Reversible formation of aryloxenium ions from the corresponding quinols under acidic conditions
Chakraborty, Mrinal,Brzozowski, Christopher F.,Novak, Michael
, p. 1236 - 1242 (2012)
Quinols, 1, are products of the hydration of O-aryloxenium ions, 2, and N-arylnitrenium ions, 3, and they are being investigated for medical uses. Under acidic conditions (pH 1-3) kinetics and products of Br- trapping demonstrate that 1a, 4-phenyl-4-hydroxy-2,5-cyclohexadienone, and 1b, 4-p-tolyl-4-hydroxy-2,5-cyclohexadienone, generate the corresponding oxenium ions 2a and 2b, respectively, as steady-state intermediates. Formation and trapping of the oxenium ions occurs in competition with the acid catalyzed dienone-phenol rearrangement. Because oxenium ion formation is reversible, the ion can only be detected by trapping with a nucleophile. Br- is an efficient trap under acidic conditions because, unlike N3 -, it is not protonated under those conditions. Attempts to detect the oxenium ions 2a and 2b at pH 4.6 and 7.1 with N3- were unsuccessful indicating that oxenium ion formation only occurs under acidic conditions. The oxenium ion 2c could not be detected under acidic conditions from the quinol 1c, 4-(benzothiazol-2-yl)-4-hydroxy-2,5-cyclohexadienone, by Br- trapping methods, even though this ion can be detected during hydrolysis of the corresponding ester, 4c. Although the benzothiazol-2-yl group is a resonance electron donor that is capable of stabilizing an O-aryloxenium ion, it is also a strong inductive electron withdrawing group that hinders the formation of 2c from 1c by decreasing the extent of protonation of 1c to generate 1cH+ and by destabilizing the transition state for ionization of 1cH+. Generation of an oxenium ion from the corresponding quinol is feasible under acidic conditions as long as the 4-substituent of the quinol is both a resonance and inductive electron donor. Copyright
Acid-catalyzed rearrangement of O-(2-arylphenyl)hydroxylamines to aryldihydroazepinones
Endo, Yasuyuki,Kataoka, Ken-Ichiro,Haga, Naoki,Shudo, Koichi
, p. 3339 - 3342 (2007/10/02)
Acid-catalyzed rearrangement of O-(2-arylpheynl) hydroxylamines followed by ring enlargement afford 7-aryl-2, 3-dihydro-1H-azepin-2-ones. 2-Amino-2-phenyl-3, 5-cyclohexadienone, an intermediate of the reaction, was trapped as the N-trifluoroacetamide.
Stabilized polyglycol for high temperatures
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, (2008/06/13)
A composition comprising a poly-alkyleneglycol is stablized against molecular degradation and viscosity loss at elevated temperatures by about 0.1 to about 10% by weight of an arylhydroquinone such as p-acetylphenylhydroquinone.