Competition between single electron transfer and nucleophilic attack. Part 2. Reaction of 2-phenyl-3H-indol-3-one with Grignard reagents

Abstract

2-Phenyl-3H-indol-3-one reacts with Grignard reagents leading both to 2,3-dihydro-2-alkyl(or phenyl)-2-phenylindol-3-ones and to 2-phenyl-3-alkyl(or phenyl)-3H-indol-3-ols; the ratio of the yields of these compounds depends on the Grignard reagent used and, to a small extent, on the reaction medium. The results are discussed in terms of competition between single electron transfer and nucleophilic attack.