ORGANIC DEUTERIUM COMPOUNDS: XV. SYNTHESIS OF SOME DEUTERATED ALKANES

An improved method of preparing deuterated alkanes from the halides has been developed. Dehalogenation of ethyl iodide, 1,1-dibromoethane, and 1,1,1-trichloroethane with zinc dust in deuterium oxide - dioxane solutions, or even with deuterium oxide alone, gave excellent yields of ethane-d 1 , ethane-1,1-d 2 , and ethane-1,1,1-d 3 . Methane-d 1 , -d 2 , -d 3 , and -d 4 were prepared similarly from methyl iodide, dibromomethane, chloroform, and carbon tetrachloride respectively. The isotopic purity of the products was over 90 mol.%. The reaction is also applicable to higher alkyl halides.