Gas-Phase Elimination Reactions of Ethers Induced by Amide and Hydroxide Ions

Article abstract of DOI:10.1021/ja00407a011

The flowing afterglow technique has been employed to study the gas-phase reactions of a series of dialkyl ethers with amide and hydroxide ions.Ethers with β-hydrogens react rapidly by elimination rather than substitution mechanisms, and they demonstrate considerable specificity in the direction of elimination.With amide ion elimination proceeds primarily by removal of the most acidic hydrogen with little or no evidence of alkoxide stability playing a role.With hydroxide ion as the base the stability of the leaving groups appears to be of some importance, and cluster ions between water and the alkoxide ions are the major products.Evidence is presented for a long-lived complex of reaction products which can react further before separating.