Output details

A new autocatalytic thioacetate-enal addition reaction: A Michael addition or not?

The Michael-addition is one of the oldest and widely used organic reactions. The accepted mechanism involves direct addition of a nucleophile to the remote carbon of the conjugated C=O. This work discovered that for the case of thioacetic acid,(and subsequently other systems) addition across unsaturated-aldehydes occurs in a multistep autocatalytic manner involving a double exotherm. This new two stage autocatalytic behaviour represents a significant discovery in a previously well established area of chemistry. The novelty of the work is due to chemical engineering methodology (adiabatic and reaction calorimetry and kinetic interpretation) combined with synthetic organic chemistry.