Reversible formation of aryloxenium ions from the corresponding quinols under acidic conditions

M Chakraborty, CF Brzozowski…

Index: Chakraborty, Mrinal; Brzozowski, Christopher F.; Novak, Michael Journal of Physical Organic Chemistry, 2012 , vol. 25, # 12 p. 1236 - 1242

Full Text: HTML

Citation Number: 3

Abstract

Abstract 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 ...

Related Articles:

Calixarenes. 7. p-Phenylcalix [4] arene

[Gutsche, C. David; No, Kwang Hyun Journal of Organic Chemistry, 1982 , vol. 47, # 14 p. 2708 - 2712]

The synthesis of 5-substituted 2, 3-dihydrobenzofurans

[Alabaster, Ramon J.; Cottrell, Ian F.; Marley, Hugh; Wright, Stanley H. B. Synthesis, 1988 , # 12 p. 950 - 952]

The hydrolysis of 4-acyloxy-4-substituted-2, 5-cyclohexadienones: Limitations of aryloxenium ion chemistry

[Novak, Michael; Glover, Stephen A. Journal of the American Chemical Society, 2005 , vol. 127, # 22 p. 8090 - 8097]

The Bromination of 4-Phenylphenyl Benzoate

[Hazlet; Alliger; Tiede Journal of the American Chemical Society, 1939 , vol. 61, p. 1447]

More Articles...