A new synthesis of hindered unsymmetrical t-Alkyl ethers

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 °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.