Diels-Alder Reactions of a Surfactant 1,3-Diene

Article abstract of DOI:10.1021/jo00007a041

The ability of aqueous micelles and reversed micelles to control the regiochemistry of Diels-Alder reactions of (E,E)-6-<<<<4-<(4-hexylphenyl)sulfonyl>-1,3-butadienyl>amino>carbonyl>oxy>-N,N,N-trimethyl-1-hexanaminium bromide (4) and 1-(4-hexylphenyl)-2-propen-1-one (2b) was evaluated.If 2b and 4 were to react within the micelles in their preferred orientations, cycloadduct 10 would result, as opposed to 6-<<<-2-cyclohexen-1-yl>amino>carbonyl>oxy>-N,N,N-trimethyl-1-hexanaminium bromide (7b) and its exo isomer 8b, the theoretically predicted products actually obtained.The orientational effects in the aggregates were not strong enough to overcome the reaction's intrinsically preferred regiochemistry.