Contrasting behaviour of (<i>E</i>)‐3‐(trimethylsilyl)‐ and (<i>E</i>)‐3‐phenylpropenoic acids towards <i>n</i> ‐butyl‐ and <i>tert</i>‐butyllithium

Abstract

Abstract The title compounds 2 and 9 react with tert ‐butyllithium to give considerable amounts of ‘anti‐Michael’ adducts 3 and 10 , respectively, in which the tert ‐butyl group is bonded to C‐2. A single‐electron‐transfer (SET) mechanism is proposed for these reactions. Both compounds behave as Michael acceptors towards n ‐butyllithium.