Synthesis of 'Push-Pull'-Oligoacetylenes

Article abstract of DOI:10.1002/hlca.19910740614

'Push-pull' triacetylenes 11a, b, c as well as 'push-pull' tetraacetylene 13b have been prepared by reaction of the corresponding trichloroene(oligoinyl)amines 9 and 10 with 2 mol-equiv. of BuLi followed by acylation.The sequences (Schemes 3 and 4) are very simple and straightforward, they could in principle be applied to the synthesis of 'push-pull' pentaacetylenes 15 and hexaacetylenes 17 (Scheme 5).Main limitations are the moderate yields as well as the low thermal stability of push-pull oligoacetylenes.