Synthese von ‘Push-Pull’-Diacetylenen

Synthesis of ‘Push-Pull’ Diacetylenes The first synthesis of push-pull diacetylenes of type 1 is described. Reaction of perchlorobutenyne ( 8 ) with two equivalents of dialkylamine, followed by dechlorination using two equivalents of butyllithium gives lithio-dialkylamino-diynes 7 . Final acylation of these intermediates leads to push-pull diacetylenes 1b–1e in good yields. The method allows the introduction of both push and pull substituents in a simple one-pot-procedure. In addition, 1a is prepared by hydroxymethylation of lithio-morpholino-diyne 7c , followed by oxidation with manganese dioxide in acetone.