Journal of Organic Chemistry p. 4198 - 4203 (1989)
Update date:2022-08-05
Topics:
Kice, John L.
Weclas-Henderson, Ludmilla
Kewan, Aly
1-Anthraquinonesulfenic acid (2) is a stable arenesulfenic acid.Its pKa, and the products and kinetics of its reactions, and those of its methyl ester (3), with both a thiol (n-BuSH) and m-chloroperoxybenzoic acid (MCPBA), have been determined.The results are compared with those for the corresponding reactions of two stable areneselenic acids (1a and 1b).The pKa of 2 (7.51) shows it to be ca. 3 pK units stronger acid than o-O2NC6H4SeOH (1a).Reaction of 2 and 3 with n-BuSH occurs at comparable rates and gives n-butyl 1-antraquinonyl disulfide (5) via a reactionthat is acid catalyzed.The rate of reaction of 2 with the thiol is ca. 104 slower than the rate of reaction of the structurally analogous areneselenenic acid, o-PhC(O)C6H4SeOH (1b).The probable reason for this large difference in rates is outlined.The difference in the rates of oxidation of 2 and 1b by MCPBA is much smaller, the selenenic acid being oxidized only 6 times faster than 2.Just as was found with selenenic acid 1a and its methyl ester, the rate of oxidation of sulfenic acid 2 by MCPBA is much faster than the rate of oxidation of its methyl ester.
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