Nickel-catalysed stereospecific cyclocarbonylation of cyclopentadiene dimer. Crystal and molecular structure of 2-(tetracyclo[5.5.1.0.0]tridec-9-en-4-yl)propionic acid

Abstract

The reaction of endo-cyclopentadiene dimer with but-2-enyl chloride, carbon monoxide, and tetracarbonylnickel in acetone–water at room temperature gives a tetracyclic acid and co-oligomers. X-Ray structural determination of the acid shows a selective cis-exo attack at the strained double bond. Some aspects of the mechanism are discussed.