The Behavior of 2-Substituted-3-hydroxyisoindolinones in the Reaction withsec-Butyllithium

This paper presents a dualistic behavior of 2‐substituted‐3‐hydroxyisoindolones in reactions with sec ‐butyllithium ( sec ‐BuLi). 2‐ tert ‐Butyl‐3‐hydroxy‐2,3‐dihydro‐1 H ‐isoindol‐1‐one ( 1a ) treated with sec ‐BuLi undergoes metalation at position 7. On the other hand, the reaction between 3‐hydroxy‐2‐phenyl‐2,3‐dihydroxyisoindol‐1‐one ( 1j ) and sec ‐BuLi results in 3‐ sec ‐butyl‐2‐phenyl‐2,3‐dihydroisiondol‐1‐one ( 3j ).