[reaction: see text] Allylic ethers are converted to the corresponding alcohol or phenol in virtually quantitative yield at temperatures below ambient simply by stirring a hydrocarbon solution of the ether with 1 molar equiv of tert-butyllithium. The reaction, which produces 4,4-dimethyl-1-pentene as a coproduct, most likely involves an S(N)2' attack of the organolithium on the allyl ether.

Allylic ethers can be converted to alcohol or phenol in nearly quantitative yield at low temperatures by stirring them with tert-butyllithium, producing 4,4-dimethyl-1-pentene as a coproduct.

Paper

Facile O-deallylation of allyl ethers via S(N)2' reaction with tert-butyllithium

References

Citations