New syntheses and chemistry of hexafluorotropone.
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.
Lou
Yan
Y
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
He
Yigang
Y
Kendall
John T
JT
Lemal
David M
DM