Experimental Evidence for an Electron-Transfer Mechanism in the Reaction between 2-Phenyl-3-(phenylimino)-3H-indole and Grignard Reagents: Application of the Marcus Theory

Article abstract of DOI:10.1021/jo00186a011

2-Phenyl-3-(phenylimino)-3H-indole reacts with 5-hexenylmagnesium bromide to give products of 1,2- and 1,4-addition and reduction.For both addition modes, the products are mixtures of 5-hexenyl- and cyclopentylmethyl-substituted derivatives.Since the 5-hexenyl radical undergoes cyclization to the cyclopentylmethyl radical, the reaction is interpreted on the basis of an electron-transfer mechanism.This is also supported by estimates of electron-transfer rate constants according to the Marcus theory.