Cyclodextrin-promoted Diels Alder Reactions of a Polycyclic Aromatic Hydrocarbon Under Mild Reaction Conditions

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2015 Dec 23

PMID 26692588

Citations 1

Authors

Sauradip Chaudhuri

Tyler Phelan

Mindy Levine

Affiliations

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Abstract

Reported herein is the effect of cyclodextrins on the rates of aqueous Diels Alder reactions of 9-anthracenemethanol with a variety of -substituted maleimides. These reactions occurred under mild reaction conditions (aqueous solvent, 40 °C), and were most efficient for the reaction of -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.

Citing Articles

An MM and QM Study of Biomimetic Catalysis of Diels-Alder Reactions Using Cyclodextrins.

Chen W, Sun L, Tang Z, Ali Z, Wong B, Chang C Catalysts. 2018; 8(2).

PMID: 29938117 PMC: 6011829. DOI: 10.3390/catal8020051.

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