New syntheses and chemistry of hexafluorotropone |
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Authors: | Lou Yan He Yigang Kendall John T Lemal David M |
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Affiliation: | Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA. |
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Abstract: | Two new routes to hexafluorotropone have been developed, one from hexachlorotropone and a superior synthesis from hexafluorobenzene. Hexafluorotropone was found to be a very weak base, with a conjugate acid pK(a) of -6.2 +/- 0.5. The tropone adds in [6 + 4] fashion to cyclopentadiene and photocyclizes to hexafluorobicyclo[3.2.0]hepta-3,6-dien-2-one. Lithium hydroxide in benzene transforms the tropone into pentafluorotropolone, which functions as a bidentate ligand. |
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