Structural and solvent control over activation parameters for a pair of retro Diels-Alder reactions.

ABSTRACT: We report the temperature dependent NMR of two Diels-Alder adducts of furan: one formed with maleic anhydride and the other with N-methylmaleimide. These adducts are the products of so-called 'click' reactions, widely valued for providing simple, reliable, and robust reactivity. Under our experimental conditions, these adducts undergo a retro Diels-Alder reaction and we use our temperature dependent NMR to determine the rates of these reactions at multiple temperatures-ultimately providing estimates of the activation parameters for the reversion. We repeat these measurements in three solvents. We find that, in all solvents, the barrier to reversion is larger for the adduct formed with N-methylmaleimide. The barrier to reversion for this adduct is relatively insensitive to changes in solven

SUBMITTER: Widstrom AL 

PROVIDER: S-EPMC6892874 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature