Journal of Organic Chemistry p. 1026 - 1029 (1986)
Update date:2022-08-30
Topics:
Doi, Joyce Takahashi
Goodrow, Marvin H.
Musker, W. Kenneth
The kinetics and mechanism of the aqueous iodine oxidation of three 3-(alkylthio)propanoates has been examined in detail.All the oxidations are essentially independent of external buffer and proceed via anchimeric assistance by the carboxylate anion.The reaction of aqueous iodine with both 3,3'-thiodipropanoate and 3-(methylthio)propanoate are enhanced a millionfold over that of simple thioethers, making these thioethers among the most easily oxidized of any reported.The degree of anchimeric assistance is considerably less with N-acetyl-S-methylcysteinate and is attributable to the lowered basicity of its carboxylate group.
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Doi:10.1055/s-2002-35561
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(1982)Doi:10.1246/bcsj.37.960
(1964)Doi:10.1039/c39780001085
(1978)Doi:10.1039/c4ra07135b
(2014)Doi:10.1039/c2ta00725h
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