The reaction of butadiene with secondary amines initiated by n-butyllithium was found to proceed selectively to produce 1-dialkylamino-cis-butene-2 under appropriate reaction conditions. For instance, diethylamine produced 1-diethylamino-cis-butene-2 in a 98–99% purity. By kinetic and spectroscopic studies, it was concluded that the lithium dialkylamide-dialkylamine (1:2) complex plays an important role in this addition reaction. The second-order rate constants of the reaction are 0.85×10−3 l/mol sec for diethylamine and 2.4×10−3 l/mol sec for diisobutylamine.
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Narita et al. (1973) studied this question.
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