DIELS-ALDER REACTIONS OF A SURFACTANT 1,3-DIENE

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-[[[[cis-6-(4-hexylbenzoyl)-cis-4-[(4-hexylphenyl)sulfonyl]-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.