F-Alkyl ethers

Preparation of symmetrical and unsymmetfical aliphatic ethers can be accomplished by coupling alkyl halides and sodium alkoxides (H illiamson). The formation of the alkoxide may be slow and incomplete because the slow-dissolving alkoxide coats the sodium. This difficulty can be overcome by using a large excess of alcohol. After the sodium has dissolved, the alkyl halide is added to form the ether which is finally removed by fractional distillation. Sodium f-butoxide is not only formed slowly but also reacts very slowly with alkyl halides. The reaction of the f-alkyl halide with the sodium alcoholate is not any better, for the chief products are olefins. Consequently, another method must be considered for preparing f-alkyl ethers (method 118). Even in the conversion of s-alkyl halides, olefin formation occurs. 

Talbot, F " Alkyl ethers as motor fuels. Proceedings of the American Petroleum Institute 44th Reftnmg Midyear... 

Dialkyl diselenides, 310 Di-f-alkyl ethers, 441 Dialkyl selenides, 310... 

---