157. Synthese von 'Push-Pull'-Diacetylenen

Article abstract of DOI:10.1002/hlca.19830660602

The first synthesis of push-pull diacetylenes of type 1 is described.Reaction of perchlorobutyne (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.