The Journal of Organic Chemistry

Heteroatom-directed allylic substitution and rearrangement reactions

JP Hagen, JJ Harris, D Lakin

Index: Hagen, James P.; Harris, Joseph J.; Lakin, Danielle Journal of Organic Chemistry, 1987 , vol. 52, # 5 p. 782 - 787

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Citation Number: 11

Abstract

Alcoholic, phenolic, and thiolic nucleophiles attack 3-chloro-1-methoxypropene (1) exclusively at C-1 in the presence of NJV-diisopropylethylamine. The reaction is formally a highly regioselective SN~' process. Some of the oxygen nucleophiles (eg, methyl salicylate) react slowly under these conditions and give poor yields; however, the corresponding lithium alkoxides, formed by treating the alcohol with lithium bis (trimethylsilyl) amide, give ...