The aldol condensation reaction and Diels-Alder reaction have been exploited in the development of green chemical transformations because of their inherent high atom economy and minimal solvent requirements.  We have developed a one pot procedure that involves the synthesis of tetraphenylcyclopentadienone (via aldol condensation of benzil and 1,3-diphenylacetone using KOH in triethylene glycol) which is then reacted without isolation with styrene to produce the Diels-Alder adduct.  Students use 1H NMR and IR analysis to determine the overall structure and speculate about the endo/exo stereochemistry.  The x-ray structure of the pentaphenylbicyclo[2.2.1]hept-2-en-7-one product was solved and provided to the students at the end of the experiment to illustrate the power of x-ray crystallography in unequivocal stereochemical structure elucidation. 

Tandem one-pot aldol condensation/Diels-Alder reaction sequence as a green synthesis  for the organic chemistry laboratory

244th National Meeting (2012)

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