title: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Goto
authors.forename: K
authors.initials: K
authors.lastname: Akimoto
authors.forename: K
authors.initials: K
authors.lastname: Aoki
authors.forename: M
authors.initials: M
authors.lastname: Shindo
authors.forename: K
authors.initials: K
authors.lastname: Koga
mesh_terms: D000478:Alkylation; D006219:Halogens / Q000737:chemistry*; D007700:Kinetics; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000737:chemistry*; D013764:Tetrahydronaphthalenes / Q000737:chemistry*; D044024:Tetralones
chemical_list: D006219:Halogens; D009281:Naphthalenes; D013764:Tetrahydronaphthalenes; D044024:Tetralones; C009423:beta-tetralone; D008094:Lithium