Allylic Rearrangements. XIII. Kinetics and Mechanisms of the Conversion of Crotyl and Methylvinylcarbinyl Chlorides to Acetates and Ethyl Ethers

Many investigators, notably Hughes, Ingold and collaborator have demonstrated that the mechanisms of nucleophilic replacement reactions at a saturated carbon atom may be classified into three general types. One mechanism, designated as S_N2 is the familiar bimolecular, usually second-order, substitution of an electron-donor such as hydroxide ion, alkoxide ion or acetate ion for the halide or a similar group as in equation (1), the replacement resulting in a complete Walden inversion