Natural and Synthetic Rubber. II. Reduction of Isoprene by Na-Nh3
Abstract The reduction of isoprene by sodium in liquid ammonia was attempted to determine: (1) whether reduction would take place in preference to polymerization and (2) the location of the added hydrogen. Isoprene was added to sodium dissolved in liquid ammonia and a 60% yield of 2-methyl-2-butene resulted. No other volatile hydrocarbon was found. High molecular weight hydrocarbons were formed but were not investigated. It is thus shown: (1) that the predominant reaction proceeds in accordance with the equation C5C8+2Na+2NH3=C5C10+2NaNH2 and (2) that hydrogen adds to isoprene in the 1,4-position, in agreement with Thiele's theory. The hydrogen addition is similar to the bromination of isoprene at low temperature. If properly conducted the latter reaction stops after 2 atoms of bromine have been added to 1 molecule of isoprene; the resulting compound, 1,4-dibromo-2-methyl-2-butene, is characterized b the inactivity of its double bond toward bromine. Similarly, 2-methyl-2-butene obtained by reduction of isoprene is not reduced to isopentane by an excess of Na—NH3 reagent.