A duality of mechanism in the hydrolysis of acyclic phosphoranes
Abstract
Acyclic phosphoranes, ArnP(OR)5–n with n= 0–3 are shown to hydrolyse in neutral conditions by an SN 1 (P) mechanism for n= 1, 2, and 3 but an SN2 (P) or addition–elimination mechanism for n= 0; this is analogous to the classical SN1 vs. SN2 mechanisms observed reactions at tetrahedral carbon.