Facile O-Deallylation of Allyl Ethers via S_N2' Reaction with tert-Butyllithium

William F. Bailey*, Michael D. England, Michael J. Mealy, Charnsak Thongsornkleeb and Lisa Teng

*Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States, Email: william.baileyuconn.edu

W. F. Bailey, M. D. England, M. J. Mealy, C. Thongsornkleeb, L. Teng, Org. Lett., 2000, 2, 489-491.

DOI: 10.1021/ol991342g

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Abstract

tert-Butyllithium induces a cleavage of allylic ethers to the corresponding alcohols or phenols in excellent yield at low temperatures in n-pentane. The reaction produces 4,4-dimethyl-1-pentene as a coproduct and most likely involves a S_N2' process, in which the organolithium attacks the allyl ether.

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Key Words

deprotection of allyl ethers

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ID: J54-Y2000