High regioselectivity in the Diels-Alder reaction of a surfactant 1,3-diene with a surfactant dienophile resulting from a short tether between their functional groups and head groups

Abstract

The Diels-Alder reaction of surfactant 1,3-diene 5 and surfactant dienophile 6 within their aqueous mixed micelles at 25(35)°C gave a 30:1 ratio of cycloadducts 14 and 15, respectively. The high regioselectivity was ascribed to a combination of alignment of 5 and 6 at the mixed micelle-H 2O interface and the short tether between their functional groups and head groups.