Monday, 26 June 2006
Ponderosa (poster/exhibit) (John Ascuaga’s Nugget Casino Resort)
59

Synthesis of 2-nitro-9-(2,2,2,-triphenylethylidene)fluorene

HyunJong Kim, Thomas W. Bell, and Rolando Procupez. University of Nevada, Reno, Reno, NV

  The title compound, which is of interest for modeling the quantum efficiency of a light-driven molecular motor, has been synthesized by two different routes from 2-nitrofluorene. A key step in the assembly of this molecule involves coupling the two aromatic moieties by addition-elimination reaction of trityl anion with a 9-methylfluorene derivative. The route explored first involves oxidation of 2-nitrofluorene to 2-nitrofluorenone. Wittig reaction with bromomethylenetriphenyl phosphorane did not succeed, apparently for solubility reasons. The synthesis was completed by reducing the nitro group, protection of the resulting amine, Wittig reaction, deprotection, and reoxidation. The shorter route, shown below, involves reaction of 2-nitrofluorene with DMF dimethyl acetal to give 2-nitro-9-methoxymethylenefluorene and displacement of methoxy by trityl anion.

 

 


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