Reduction by dissolving metals. Part XVII. Metal–ammonia reductions of some conjugated dienamines

Abstract

Reductions with lithium in ammonia, in the presence or absence of t-butyl alcohol, of 1-morpholino- and 1-dimethylamino-cyclohexa-1,3-dienes result in monoenamines, chiefly the 1-enes. A minor proportion of the cyclo-hexane derivative is formed in several cases. With an unsymmetrical ring the reduction gives products with the 1-double bond in both alternative positions, so the method cannot be used to produce one isomer only. No hydrogenolysis of the amine group occurs, but complete loss of OMe is found with 4-methoxycyclohexa-1,3-di-enylmorpholine.