The influence of micelles on Diels-Alder reactions

In summary, all studies on the influence of micelles on himolecular Diels-Alder reactions indicate that the apparent rate constants in these media are strikingly similar to the rate constants in water. 

Unfortunately, more detailed kinetic studies aimed at the determination of the second-order rate constants in the micellar pseudophase have not been published. 

Analogously, the effect of micelles on the rate of the unimolecular retro Diels-Alder reaction has been studied. Also here only a modest retardation or acceleration is observed. Likewise, the presence of micelles has been reported to have a modest influence on an intramolecular Diels-Alder reaction . Studies on the endo-exo selectivity of a number of different Diels-Alder reactions in micellar media lead to comparable conclusions. Endo-exo selectivities tend to be somewhat smaller in micellar solutions than in pure water, but still are appreciably larger than those in organic media In contrast, in microemulsions the endo-exo selectivity is reduced significantly  

Jaeger and co-workers studied the regioselectivity of the reaction of a surfactant diene with a surfactant dienophile in micellar media . The orientational effects in the aggregates could result in an increase in the regjoselectivity in aqueous solutions of these compounds as compared to the reaction in organic media. 

The use of dienophile 5.1 also allows study of the effect of micelles on the Lewis-acid catalysed reaction. These studies are described in Section 5.2.2. and represent the first in-depth study of Lewis-acid catalysis in conjunction with micellar catalysis , a combination that has very recently also found application in synthetic organic chemistry .  

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