AOT-based microemulsions accelerate the 1,3-cycloaddition of benzonitrile oxide to N-ethylmaleimide.
We studied the 1,3-dipolar cycloaddition of benzonitrile oxide to N-ethylmaleimide in AOT/isooctane/water microemulsions at 25.0 degrees C and found the reaction rate to be roughly 150 and 35 times greater than that in isooctane and pure water, respectively. The accelerating effect of the microemulsion is the combined result of an increase in the local concentrations of the reactants through incorporation into the interface and of the intrinsic rate of the process through electrostatic interactions with the headgroups in the surfactant.
Engberts
J B F N
JB
Physical Organic Chemistry Unit, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Fernandez
E
E
García-Río
L
L
Leis
J R
JR