Journal of Organic Chemistry p. 4 - 10 (1985)
Update date:2022-08-16
Topics:
Williams, Keith A.
Doi, Joyce Takahashi
Musker, W. Kenneth
The kinetics of the aqueous iodine oxidation of a number of imidazolyl- and benzimidazolylalkyl methyl sulfides have been studied.Evidence of neighboring-group participation has been observed in all cases.The anchimeric assistance provided by the benzimidazole moiety is evidenced by rate accelerations of 102-105.The oxidation of 1-methyl-2-<3-(methylthio)propyl>imidazole, 1, is 106 times faster than that of simple thioethers and is faster than any previously reported acyclic thioether.The reaction of 2-<3-(methylthio)propyl>benzimidazole is accelerated by105 via a transient N-S dication.Additionally, the pH profiles of all of the compounds studied provide strong evidence for N-S interacted intermediates.
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