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 ...
