Issue Date: February 7, 2011
Meet The Ivyanes
Chemists in Australia have given birth to a new family of hydrocarbons: the ivyanes. These oligocyclopropanes feature triangular rings hanging off the side of a carbon chain, a structure that resembles leaves on an ivy vine (Chem. Sci., DOI: 10.1039/c0sc00500b). In 2009, Michael S. Sherburn and coworkers at Australian National University reported the synthesis of dendralenes, a class of compounds in which each carbon in a chain is part of a branching alkene ideally situated to undergo cyclopropanation. Sherburn’s group has now used the Simmons-Smith reagent (diiodomethane and diethylzinc) to convert dendralenes with from three to eight alkenes to the corresponding ivyanes. The reactions are a chemical tour de force. For example, conversion of dendralene to ivyane involves formation of 16 C–C bonds. The shorter chain ivyanes are liquids at room temperature, whereas the  and  versions are solids. The compounds adopt chiral helical conformations in both solution and solid phases, a property that could be exploited in multiple applications. In addition, the unique ivyane framework prompted the team to try ring-opening reactions, which led to dimethyl-substituted chains with contiguous quaternary carbons, structures that are normally tough to make.
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