Models for the Ion-Pair Cluster Mechanism in Nucleophilic Substitution Reactions

Article abstract of DOI:10.1021/jo00330a031

Several bis(alkoxytriphenylphosphonium) salts have been prepared.When sterically constrained, as close neighbors, the leaving groups of these cations react rapidly at room temperature with negative nucleophiles to produce the expected substitution product.When sterically unconstrained, these types of functional groups behave as if they were mono(alkoxytriphenylphosphonium) salts, substituting very slowly or not at all at room temperature.The ion-pair cluster mechanism is discussed in light of these results.