Attempted Synthesis of Push-Pull Diacetylenes

Article abstract of DOI:10.1002/hlca.19830660511

Two alternative synthesis of push-pull diacetylenes of type 1 (5-amino-2,4-alkadiynals) are investigated.A bromination-dehydrobromination sequence starting with 5-dimethylamino-2,4-pentadienal (2) as well as application of the well-known Cadiot-Chodkiewicz coupling reaction give intermediates 3-5, and 7 and 8, respectively, but fail to give the target molecules 1.