Rate Enhancement with High Ratio of the Monoalkylated Product to the Dialkylated Product in the Alkylation of the Lithium Enolate of 1-Tetralone with Reactive Alkyl Halides

Abstract

The reactions of the lithium enolate of 1-tetralone with reactive alkyl halides were examined in the absence and in the presence of 3 eq of various ligands for the lithium. It is shown that the rates of the reactions are enhanced greatly in the presence a tetradentate amine (1, 1, 4, 7, 10, 10-hexamethyltriethylenetetramine), and the ratio of the monoalkylated product to the dialkylated product is increased under shorter reaction times.