Regioselectivity control in a Diels-Alder reaction of a surfactant 1,3- diene with a surfactant dienophile

Article abstract of DOI:10.1016/S0040-4039(98)02350-8

The Diels-Alder reaction of surfactant 1,3-diene 1 and surfactant dienophile 2 within aqueous mixed micelles at 25°C gave a 6.6:1 ratio of cycloadducts 11 and 12, and that of nonsurfactant analogues 10 and 13 in C₆H₅Me at 75(85) °C gave a 1:l ratio of cycloadducts 14 and 15. The regioselectivity of the reaction of 1 and 2 was controlled by their alignment at the mixed micelle-H₂O interface.