Neighboring-Group Participation in Organic Redox Reactions. 10. The Kinetic and Mechanistic Effects of Imidazole and Benzimidazole Nitrogen on Thioether Oxidations
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-imidazole, 1, is 106 times faster than that of simple thioethers and is faster than any previously reported acyclic thioether.The reaction of 2-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.
Williams, Keith A.,Doi, Joyce Takahashi,Musker, W. Kenneth
p. 4 - 10
(2007/10/02)
More Articles about upstream products of 4198-64-5