Reaction of lithium metal with benzil in THF. A kinetic study

Abstract

Abstract The kinetics of benzil reduction by lithium metal in THF were investigated under different reaction conditions. The main reaction products were phenylacetophenone and bibenzyl; 1,2‐diphenylethanol and diphenylethene were minor products. The first radical anion intermediate formed by electron transfer upon chemisorption of the benzyl on the metal surface was fully characterized and quantitatively determined by ESR spectroscopy. The kinetics of the benzil decay and of the formation of the two main products were followed by GC and ESR. A unique feature of this reaction is the presence of a well‐defined and reproducible induction period. A mechanism is proposed which accounts for the main experimental observations. Copyright © 2003 John Wiley & Sons, Ltd.