ADVERTISEMENT
2 /3 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

Meet The Ivyanes

Chemists create a new family of hydrocarbons in which cyclopropane rings hang off the sides of carbon chains

by Stephen K. Ritter
February 7, 2011 | APPEARED IN VOLUME 89, ISSUE 6

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 [8]dendralene to [8]ivyane involves formation of 16 C–C bonds. The shorter chain ivyanes are liquids at room temperature, whereas the [7] and [8] 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.

X

Article:

This article has been sent to the following recipient:

Leave A Comment

*Required to comment