Optimization of Diels-Alder Reactions in Fluorous and Non-fluorous Solvents

The use of fluorous solvents in Diels-Alder reactions have been identified as a viable means to optimize the reaction’s stereoselectivity. Past research on the use of fluorous solvents in Diels-Alder reactions suggest that the characteristics of fluorous solvents (including their tendency to be both liphophobic and hydrophobic) may provide optimal conditions for Diels-Alder reactions. This study investigates these characteristics by comparing the effects of these solvents and other solvents (or the lack thereof) on the Diels-Alder reaction. The use of the fluorous solvent FC-70 was also studied for the purpose of cracking dicyclopentadiene. Literature on molecular interactions and on Diels Alder reactions is utilized to explain how the structural and chemical features of fluorous solvents influence reaction efficiency and selectivity, and how reaction conditions (heat and duration of reaction) alter the efficiency and selectivity. We use structural and thermodynamic arguments to explain these alterations. By better understanding how fluorous solvents function in Diels-Alder reactions, reaction conditions may be improved and their use expanded.