Enhancing 2-iodoxybenzoic acid reactivity by exploiting a hypervalent twist.
A rearrangement of hypervalent bonds, or twisting, proves to be the rate-determining step in the 2-iodoxybenzoic acid (IBX) oxidation of alcohols. From this insight, derived from density functional theory calculations, we explain why IBX oxidizes large alcohols faster than small ones and propose a modification to the reagent predicted to make it more active.
Su
Julius T
JT
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.
Goddard
William A
WA
D004735:Energy Transfer; D006860:Hydrogen Bonding; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014867:Water / Q000737:chemistry
D007462:Iodobenzenes; D007463:Iodobenzoates; D014867:Water; C476101:o-iodoxybenzoic acid; D000432:Methanol