Neighboring-group participation in organic redox reactions. 10. The kinetic and mechanistic effects of imidazole and benzimidazole nitrogen on thioether oxidations

KA Williams, JT Doi, WK Musker

Index: Williams, Keith A.; Doi, Joyce Takahashi; Musker, W. Kenneth Journal of Organic Chemistry, 1985 , vol. 50, # 1 p. 4 - 10

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Citation Number: 15

Abstract

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 lo2-lo6. The oxidation of l-methyl- 2-[3-(methylthio) propyl] imidazole, 1, is le times faster than that of simple thioethers and is ...