1, 3-Diphehyl-l, 3-butadiene 3 has been found to rapidly undergo the Diels-Alder reaction at room temperature to yield 1, 3, 4-triphenyl-4-styrylcyclohexene 10. The dimer was characterized by elemental analysis, infrared and nuclear magnetic resonance spectrosopy. The isomeric diphenylbutadienes were of interest as a model system to study the interaction of steric hindrance and electronic effects in the homopolymerization of disubstituted butadienes. Several synthetic routes to an appropriate tosylate for base catalyzed elimination at low temperatures to avoid dimerization of the monomer were explored and found unsuccessful for various reasons. The monomer was trapped as an iron tricarbonyl complex. This complex as well as the hydrochloride of the iron tricarbonyl complex were found to be easily air oxidized in solution.
Allen, David, "Polymerization of Disubstituted Conjugated Dienes: Synthesis of 1, 3-Diphenyl-1, 3-Butadiene" (1982). Thesis. Rochester Institute of Technology. Accessed from
RIT – Main Campus