Hexafluorocyclohexane Sets A Polarity Record

Credit: Courtesy of Neil Keddie

Credit: Courtesy of Neil Keddie

Chemists this year made the all-cis isomer of 1,2,3,4,5,6-hexafluorocyclohexane, a crystalline ring molecule with all six fluorines pointing “up” and all six hydrogens pointing “down.” This compound, produced by David O’Hagan, Neil S. Keddie, and coworkers of the University of St. Andrews, is remarkable for having a dipole moment of 6.2 debyes, making it the most polar nonionic aliphatic compound known to exist (Nat. Chem. 2015, DOI: 10.1038/nchem.2232). The deceptively simple molecule was a complex synthetic target because it required 12 steps to make and has nine possible isomers that can adopt up to 15 conformations.

Synthesis of the very polar all-cis hexafluorocyclohexane proceeds in 12 steps via a dianhydroinositol intermediate.

Synthesis of the very polar all-cis hexafluorocyclohexane proceeds in 12 steps via a dianhydroinositol intermediate.

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