3 years ago

On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents

On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents
Despite the remarkable rate acceleration under protic solvents such as alcohols and water, the use of acrylates as activated alkenes places a problem due to the possibility of ester hydrolysis or transesterification. Therefore, the tandem transesterification/Morita-Baylis-Hillman (MBH) reactions were investigated by ESI(+)-MS/(MS) and 1H NMR techniques. For the first time, the MBH back-reaction was fully examined by ESI(+)-MS/(MS) using labelling reagents revealed the complex equilibrium involving the Michael-type addition step of DABCO to acrylate. C- and O-protonation were observed at this stage, showing the transesterification process occurs previous to the aldol step, which is the rate-determining step of the mechanism. At this stage, a short-lived tetrahedral intermediate might be involved and should be considered in these processes.

Publisher URL: www.sciencedirect.com/science

DOI: S0022286017313704

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