An addition reaction of diethylamine onto isoprene catalyzed by lithium diethylamide was found to produce selectively 1-diethylamino-3-methyl-2-butene. The regioselectivity of this addition reaction is compared to the results with the sodium amide catalyst system. On the basis of kinetic studies, the comparison of the reactivity of isoprene with that of butadiene is discussed in connection with the initiation reaction of these monomers in anionic polymerization. It is also concluded that the activation of lithium diethylamide by diethylamine causes the rapid addition reaction of the amide anion onto diene and styrene, in contrast with the extremely slow initiation reaction in the polymerizations of these monomers with lithium diethylamide as catalyst in polar solvents.
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Narita, T., Nitadori, Y. & Tsuruta, T. Reactivity of Isoprene toward Lithium Diethylamide— Diethylamine Complex. Polym J 9, 191–194 (1977). https://doi.org/10.1295/polymj.9.191
- Lithium Diethylamide
- Addition Reaction
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