5]Radialene Fills In Hydrocarbon Gap

Abstract

Radialenes are a unique class of star-shaped cyclic hydrocarbons that have double bonds radiating out from each carbon in the ring. Chemists have made the three-, four-, and six-membered ring versions of these polyenes in the past, but never [5]radialene. It has always been deemed too unstable. An Australian research team including Emily G. Mackay and Michael S. Sherburn of Australian National University and Michael N. Paddon-Row of the University of New South Wales has done a little computational detective work to find out why. Using the clues they turned up, the researchers developed a synthetic strategy to make [5]radialene for the first time. “The structure and properties of [5]radialene are of great interest for chemists, not only from a synthetic perspective, but also for the physical organic chemistry of the molecule,” comments Norihiro Tokitoh of Kyoto University, in Japan, whose group has synthesized radialenes. “With this missing molecule in ...