Synthesis and properties of the ivyanes: the parent 1,1-oligocyclopropanes

Abstract

Practical syntheses of the first six members of the ivyane (1,1-oligocyclopropane) family of fundamentalhydrocarbons have been achieved from the cross-conjugated polyenes known as dendralenes. Evidencefor helical conformations in both the solid state and in solution is presented. [6]Ivyane exhibits one ofthe highest experimental heats of combustion recorded for a hydrocarbon. Ring-opening reactions ofivyanes furnish new and interesting structures that are difficult to access by conventional means.