A one-step alternative to the Grignard reaction

Abstract

The reactions of organic halides with carbonyl compounds in the presence of lithium or sodium and with tetrahydrofuran as solvent have been studied. When lithium is used alcohols are formed in high yield which in many cases exceed those obtained by the analogous Grignard reaction. The process involves the intermediate formation of organo-lithium species. With sodium, the yield of alcohol is significantly reduced and with carbonyl compounds possessing α-hydrogen atoms, hydrogen abstraction by the intermediate organo-sodium species predominates. The effect of the addition of electron-transfer reagents such as naphthalene or biphenyl to the sodium system has been studied and the yields of alcohols have been shown to increase with the concentration of additive present.