Cyclodextrin-promoted Diels Alder reactions of a polycyclic aromatic hydrocarbon under mild reaction conditions. Issue 13 (25th March 2015)

• Record Type: Journal Article
• Authors: Chaudhuri, Sauradip; Phelan, Tyler; Levine, Mindy
• Is Part Of: Tetrahedron letters. Volume 56:Issue 13(2015)
• Page Start: 1619
• Page End: 1623
• Publication Date: 2015-03-25
• Subjects: Cyclodextrin -- Supramolecular catalysis -- Diels–Alder -- Maleimide -- Polycyclic aromatic hydrocarbons; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.185
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Reported herein is the effect of cyclodextrins on the rates of aqueous Diels Alder reactions of 9-anthracenemethanol with a variety of N -substituted maleimides. These reactions occurred under mild reaction conditions (aqueous solvent, 40 °C) and were most efficient for the reaction of N -cyclohexylmaleimide with a methyl-β-cyclodextrin additive (94% conversion in 24 h). 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.