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Topic: Synthesis of triphenylfluoranthene  (Read 2336 times)

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Offline zodiacfire

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Synthesis of triphenylfluoranthene
« on: June 22, 2009, 04:11:03 PM »
I'm attempting the synthesis of 7,9,10-triphenyl fluoranthene in two steps.
The first step is a double Knoevenagel condensation of diphenyl acetone with acenaphthene quinone, dissolving 1 equivalent of each reactant in hot pure ethanol and then adding a mixture with a ratio 3g KOH/15 mL EtOH for 0.1 equivalents of reagents and holding at reflux for 1 hour.  The two reagents are yellow and the solution turns black immediately upon addition of the ethanolic KOH.  I filter and recrystallize the product of this reactant (henceforth called the "intermediate"), which is a dark charcoal color.  This intermediate is a diphenyl cyclopentadienone with an acenaphthyl group.  I ran proton and C13 NMR as well as DSC; they all seem consistent with a pure product. 

My problem seems to be coming from the following second step: a Diels-Alder reaction between the intermediate and phenylacetylene.  This is supposed to eliminate the ketone oxygen and one carbon from the acetylene as CO, while adding a sixth carbon into the central ring along with the phenyl group.  The one and only publication I have as reference gives almost no details, but suggests using xylenes (optional) as a solvent for this next step.  Professors in the department have suggested various conditions for this reaction.  Online references suggest temperatures ranging from -78 C to 150 C and reaction times from 1-100 hours. 

I would appreciate any and all help trying to figure out optimal conditions, including time, temperature, relative amounts, etc.  Thanks very much.  If I did a poor job explaining the situation, it's because I am far from an organic chemist!!  I will attempt to provide better details if someone is willing and able to help.

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