Journal of the American Chemical Society p. 1244 - 1248 (1982)
Update date:2022-08-18
Topics:
Steenken, S.
Neta, P.
Alkyl radicals substituted at Cα by alkyl, carboxyl, hydroxyl, alkoxyl, and chlorine react in aqueous solutions with IrIVCl62- to yield Ir(III) species.In the case of substitution by hydroxyl and alkoxyl, the rate constants are in the diffusion-controlled range ((4-6)x109 M-1 s-1) and the reaction proceeds by electron transfer.In the case of ethyl, methyl, carboxymethyl, and chloromethyl radicals the rate constants range from 3.1x109 for ethyl to 2.8x107 M-1 s-1 for trichloromethyl and the reaction proseeds by chlorine transfer from IrCl62- to the alkyl radical.With isopropyl and tert-butyl radicals the reaction proceeds by both electron and chlorine transfer.Alkyl radicals also react with Fe(CN)63-.The rate constants increase strongly with increasing alkylation at Cα from 5x106 for methyl to 3.6x109 M-1 s-1 for tert-butyl, indicating that the transition state for the reaction is highly polar.Rate constants for reaction of MnO4- with alkyl radical are of the order 109 M-1 s-1.
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