A New Synthesis of Hindered Unsymmetrical t-Alkyl Ethers

Article abstract of DOI:10.1246/cl.1991.1739

The unusual Williamson reactions of t-butyl and t-pentyl halides with lithium t-alkoxides or with t-alkyl alcohols and amines were carried out at 20-50 deg C.Some of the nucleophilic substitution products were new unsymmetrical ethers: t-butyl t-pentyl ether, t-butyl 1,1-dimethyl-2-propenyl ether, t-butyl 1,1-dimethyl-2-propynyl ether, 1,1-dimethyl-2-propynyl t-pentyl ether, and t-butyl 1-ethyl-1-methyl-2-propynyl ether.