Sauradip Chaudhuri - Cyclodextrin-promoted Diels Alder reactions of a polycyclic aromatic hydrocarbon under mild reaction conditions

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      Publication Details (including relevant citation   information):

        Tetrahedron Lett. 2015 Mar 1; 56(13): 1619–1623

      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   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.

      Address (URL): http://www.sciencedirect.com/science/article/pii/S004040391500235X