Elucidation of the Complex Baylis-Hillman Reaction of 3-Methoxy-2-nitrobenzaldehyde with Methyl Vinyl Ketone

DABCO-catalyzed reaction of 3-methoxy-2-nitrobenzaldehyde with methyl vinyl ketone (MVK) affords a mixture of products, comprising the ‘normal’ Baylis-Hillman adduct, the MVK dimer and a pair of diastereomeric bis-(MVK) Baylis-Hillman adducts. 1H NMR spectroscopy-based kinetic studies have provided clear insights into the competing pathways and product distributionin this complex reaction.Keywords: Baylis-Hillman reaction, mechanism, kinetics, 1H NMR spectroscopic analysis, bis-(MVK)Baylis-Hillman product