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The effect of micelles of sodium dodecyl sulfate (SDS), cetyltrimethylammonium bromide (CTAB), dodecyl heptaoxyethylene ether (C12E7), and copper and zinc didodecyl sulfate (M(DS)2) on the Diels−Alder reaction of 3-(para-substituted phenyl)-1-(2-pyridyl)-2-propen-1-ones 1a−g, containing neutral, cationic, or anionic substituents, with cyclopentadiene (2) has been studied. In the absence of catalytically active transition-metal ions, micelles invariably retard the reaction. This can be rationalized on the basis of different binding locations of the reaction partners in the micelle. These binding sites have been probed using solubilizate-induced aromatic shifts in the 1H NMR spectrum of the surfactant and paramagnetic counterion-induced relaxation enhancements of the 1H NMR signals of the solubilizate. In contrast to SDS, CTAB, and C12E7, Cu(DS)2 micelles catalyze the Diels−Alder reaction between 1 and 2 with extremely high efficiency, leading to rate enhancements up to 1.8 × 106 compared to the uncatalyzed...

Million-Fold Acceleration of a Diels−Alder Reaction due to Combined Lewis Acid and Micellar Catalysis in Water