The cobalt catalyzed [4 + 2 + 2] cycloadditions of bicyclo[2.2.2]octadiene and several benzobarrelenes are reported, marking the first [4 + 2 + 2] cycloadditions of these homoconjugated dienes. The [2 + 2 + 2] reaction of benzobarrelene with diphenylacetylene was also successful. (C) 1999 Elsevier Science Ltd. All rights reserved.