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1978, Vol.51, No.3
866-868
Synthesis of Hindered t-Alkyl Ethers
1 Department of Industrial Chemistry, Faculty of Engineering, Kanazawa University
Abstract
Di-t-butyl ether was prepared in 6–73% yields by the reactions of t-butyl halide with Ag2CO3, Ag2O, HgO, ZnO, ZnCO3, PbO2, Cu2(CO3)(OH)2, and Tl2O3 at 20–65 °C in hydrocarbons under nitrogen. Similar reactions gave seven new hindered di-t-alkyl ethers: di-t-pentyl ether, bis(1,1-dimethylbutyl) ether, bis(1-ethyl-1-methylpropyl) ether, bis(1,1-dimethylpentyl) ether, bis(1-ethyl-1-methylbutyl) ether, bis(1,1-diethylpropyl) ether, and bis(1,1-dimethylhexyl) ether. The yield of di-t-alkyl ether decreased as the t-alkyl group became bulky. A slight difference in the skeletal structure of the t-alkyl halide markedly influences the substitution. The reaction pathways are elucidated on the basis of the experimental results.
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