Reaction of Allylic and Benzylic Methyl Ethers with Sodium and Trimethylchlorosilane. Evidence for the Intermediacy of Allylic Radicals and Anions

Article abstract of DOI:10.1021/jo00315a007

Allyl methyl ether and benzyl methyl ether react with sodium and trimethylchlorosilane to yield, respectively, allyltrimethylsilane and benzyltrimethylsilane. α,α-Dimethylallyl methyl ether and γ,γ-dimethylallyl methyl ether react with sodium and trimethylchlorosilane to yield γ,γ-dimethylallyltrimethylsilane. α-Methylallyl methyl ether and trans-γ-methylallyl methyl ether react with trimethylchlorosilane and sodium to yield similar product mixtures of α-methylallyltrimethylsilane and cis- and trans-γ-methylallyltrimethylsilane.These results are discussed in ter ms of a mechanism involving electron transfer to yield allylic radicals and allylic anion intermediates.