REGIOSELECTIVITY OF DIELS-ALDER REACTIONS OF A SURFACTANT 1,3-DIENE WITH SURFACTANT DIENOPHILES

The ability of aqueous surfactant aggregates to control the regiochemi stry of Diels-Alder reactions was investigated with surfactant 1,3-die ne n-2-yl]thio]phenyl]-N,N,N-trimethyl-1-butanaminium bromide (6), der ived in situ by thermal extrusion of SO2 from n-3-yl]thio]phenyl]-N,N, N-trimethyl-1-butanaminium bromide (8), and surfactant dienophiles eny l]carbonyl]-oxy]-N,N,N-trimethyl-1-hexanaminium bromide (7) (a, R = Me ; b, R = Bu; c, R = C8H17). In each case an excess of yl)-5-[[6-(trime thylammonio)hexoxy]carbonyl]-1-cyc lohexene dibromide (16) over lammon io)hexoxy]carbonyl]-5-(alkoxycarbonyl)-1-cyc lohexene dibromide (17) w as obtained, consistent with the reaction of 6 and 7 within a mixed ag gregate in their preferred orientations at the aggregate-H2O interface . The cyclohexene rings of 16 and 17 have different conformational cha racter in chloroform resulting from supramolecular effects within reve rsed micelles.