Journal of the American Chemical Society, Vol.122, No.19, 4569-4572, 2000
Two-electron transfer from potassium anion to peroxides: Simultaneous or stepwise?
Reaction of the two-electron donor K(+)Crown K- with phenylacetyl peroxide produces phenylacetic acid, toluene, bibenzyl, and benzyl phenylacetate. The formation of products derived from benzyl radical shows that some electron transfers must be stepwise and that the second electron transfer, although Very exothermic, is fast but not exceedingly so. This conclusion is supported by control experiments with sodium naphthalenide, sodium biphenylide, and Nd as reductants, and with benzoyl peroxide.