9,9,10,10-tetrafluorophenanthrene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the 9,9,10,10-tetrafluoro-9,10-dihydrophenanthrene (1.96 g, 7.75 mmol) in THF (15 ml) was treated with 30% aqueous NH4OH (30 ml) and zinc (2.52 g, 38.75 mmol) and stirred under N2 for 24 hours at room temperature. The reaction was monitored by GC/MS for disappearance of the starting material and found to be complete. The solution was filtered, extracted with hexane (30 ml), and filtered through a short silica column (20 g). The hexane solution was evaporated in vacuo to afford an oil. This crystallized on cooling to room temperature to afford 1.58 g (95% yield) of product. The solution was filtered extracted with hexane (30 ml) filtered through a short silica column (20 g) The hexane solution was evaporated in vacuo to afford an oil This crystallized on cooling to room temperature