The reaction of amines with conjugated dienes in the presence of alkali naphthalenide. A new synthesis of geranyl acetate

Abstract

Reaction of a conjugated diene with diethylamine using sodium naphthalenide in tetrahydrofuran gives a mixture of β,γ-unsaturated amines. From myrcene, N,N-diethyl-2-ethylidene-6-methylhept-5-enylamine, N,N-diethylnerylamine and N,N-diethylgeranylamine are obtained. Reaction of β,γ-unsaturated amines with acetic anhydride gives a mixture of β,γ-unsaturated acetates. From N,N-diethylgeranylamine, a mixture of neryl acetate and geranyl acetate is obtained.