Abstract
We examine the reaction of ethanol with glyoxal to form hemiacetal by means of the high-level G4(MP2) procedure. In this reaction, an intermolecular proton transfer is coupled with the formation of a covalent CO bond between the two molecules. We find a novel catalytic reaction mechanism in which an H2SO4 catalyst reduces the barrier height from ∆H‡298=140.2 to 16.3kJmol−1. It is well established that H2SO4 can effectively catalyse intramolecular proton transfers. This letter shows that H2SO4 can catalyse an intermolecular proton transfer that is coupled with a covalent bond formation.
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