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.
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.
Goto
M
M
Graduate School of Pharmaceutical Sciences, University of Tokyo, Japan.
Akimoto
K
K
Aoki
K
K
Shindo
M
M
Koga
K
K
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
D006219:Halogens; D009281:Naphthalenes; D013764:Tetrahydronaphthalenes; D044024:Tetralones; C009423:beta-tetralone; D008094:Lithium