Facile O-deallylation of allyl ethers via S(N)2' reaction with tert-butyllithium
[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.
Bailey
WF
Department of Chemistry, University of Connecticut, Storrs 06269-3060, USA. bailey@uconn.edu
England
MD
Mealy
MJ
Thongsornkleeb
C
Teng
L