Synthesis and reactivity of electron poor allenes: formation of completely organic frustrated Lewis pairs

Abstract

The synthesis of several electron poor allenes bearing electron withdrawing substituents is described and their use as Lewis acids in the field of frustrated Lewis pair (FLP) chemistry reported. At room temperature the combination of N-heterocyclic carbenes (NHC) with the allenes under study invariably afforded the corresponding Lewis adducts; however, at −78 °C this reaction is in most of the cases inhibited and kinetically induced organic FLPs are formed. Under these conditions the activation of S–S bonds in disulfides has been achieved in excellent yields.