Synthesis of Alkynylcyclooctatetraenes and Alkynylcubanes

Article abstract of DOI:10.1021/jo00017a028

The coupling of a variety iodocubanes with terminal acetylenes in refluxing NEt3 in the presence of Cu(I) and Pd(0) were examined.The products, isolated in about 50percent yields, were not alkynylcubanes but were instead the first examples of alkynyl-1,3,5,7-cyclooctatetraenes.The first examples of alkynylcubanes (cubylacetylenes) were themselves synthesized in modest yields by Negishi's procedure from alkyl cubyl ketones.Cubylacetylenes were shown to be stable under Heck-like coupling conditions and potentially useful thereby for the introduction of the cubylacetylene moiety into complex systems.