title: Cyclodextrin-promoted Diels Alder reactions of a polycyclic aromatic hydrocarbon under mild reaction conditions.
abstract: Reported herein is the effect of cyclodextrins on the rates of aqueous Diels Alder reactions of 9-anthracenemethanol with a variety ofN-substituted maleimides. These reactions occurred under mild reaction conditions (aqueous solvent, 40 °C), and were most efficient for the reaction ofN-cyclohexylmaleimide with a methyl-β-cyclodextrin additive (94% conversion in 24 hours). These results can be explained on the basis of a model wherein the cyclodextrins bind the hydrophobic substituents on the maleimides and activate the dienophile via electronic modulation of the maleimide double bond. The results reported herein represent a new mechanism for cyclodextrin-promoted Diels Alder reactions, and have significant potential applications in the development of other cyclodextrin-promoted organic transformations. Moreover, the ability to deplanarize polycyclic aromatic hydrocarbons (PAHs) under mild conditions, as demonstrated herein, has significant applications for PAH detoxification.
authors.affiliation: Department of Chemistry, University of Rhode Island, 51 Lower College Road, Kingston, RI 02881.
authors.forename: Sauradip
authors.initials: S
authors.lastname: Chaudhuri
authors.affiliation: Department of Chemistry, University of Rhode Island, 51 Lower College Road, Kingston, RI 02881.
authors.forename: Tyler
authors.initials: T
authors.lastname: Phelan
authors.affiliation: Department of Chemistry, University of Rhode Island, 51 Lower College Road, Kingston, RI 02881.
authors.forename: Mindy
authors.initials: M
authors.lastname: Levine
keywords: Diels-Alder; cyclodextrin; maleimide; polycyclic aromatic hydrocarbons; supramolecular catalysis