Substitutions nucleophiles d'amines sur les halogeno-1 cycloalcenes en presence de bases dans le tetrahydrofuranne

Condensations of amines with 1-chloro cycloheptene in the presence of complex base (NaNH₂-t-BuONa) lead to mixtures of enamines and 1,2-cycloheptadiene dimer. Under the same conditions, 2-chloro and 3-chloro bicyclo 3.2.1] oct-2 enes yield only enamines via bicyclo 3.2.1] oct-2 yne. The mechanism of these reactions depends not only upon the halogeno derivatives but also upon “reaction media.” The general problem of the interpretation of elimination-addition reactions is discussed.