131906-71-3Relevant academic research and scientific papers
Diels-Alder Reactions of a Surfactant 1,3-Diene
Jaeger, David A.,Shinozaki, Hiraku,Goodson, Patricia A.
, p. 2482 - 2489 (2007/10/02)
The ability of aqueous micelles and reversed micelles to control the regiochemistry of Diels-Alder reactions of (E,E)-6--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.
