Water-mediated organic reactions significantly contribute
to the
protection of the environment. Desymmetrization reactions, which convert
only one of the identical functional groups within one molecule, are
cost-effective because of the low cost of the starting materials.
In combination with these two merits, highly efficient and practical
selective monohydrolysis reactions of symmetric diesters were previously
reported. The products of these reactions are versatile building blocks.
The mechanisms of this reaction are hypothesized to proceed through
micellar aggregates in which the hydrophilic carboxylate anions formed
by monohydrolysis are directed outward and the remaining hydrophobic
groups are directed inward in governing the selectivities. Here, dynamic
light scattering and electrophoretic light scattering experiments
were performed for detection of the key intermediates in the reaction.
These experiments revealed the existence of aggregates with negative
charges on the surface in the mainly aqueous media, supporting the
reaction mechanisms that control the high selectivities.