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

Org Lett. 2000 Feb 24;2(4):489-91. doi: 10.1021/ol991342g.

Abstract

[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.