Eisleb alkylation

What is Eisleb alkylation?

The Eisleb reaction, first reported in 1941 by Eisleb, involves the alkylation of compounds containing active hydrogen with alkyl halide through treatment with sodium amide NaNH2.

Eisleb alkylation - general reaction scheme
Eisleb alkylation
  • R1 , R1 = aryl, alkyl-C(O), alkyl-SO2, CN
  • R = alkyl
  • X = Cl, Br, I

The types of compounds that contain active hydrogens include deoxybenzoin, diphenylmethane, phenylacetonitrile, fluorene, benzyl phenyl sulfone, and 2-pyridyl acetonitrile. Generally, this reaction leads to the introduction of an N,N-dialkylamino alkyl group to compounds that contain an active proton, and a satisfactory yield can be obtained.

Compounds that contain active hydrogens can be alkylated using this reaction.