Analogies between nucleophilic substitutions at silicon and phosphorus: kinetic and stereochemical studies of five- and six-membered ring oxasilacycloalkanes
Abstract
A kinetic study of hydrolysis and methanolysis of the five-membered ring oxasilacyclopentane (I) shows a very large rate acceleration relative to the six-membered ring and open-chain analogues (II) and (III), the reactions occurring with inversion of configuration; this further analogy between nucleophilic substitutions at silicon and phosphorus suggests a similar mechanism for both processes.