South African Journal of Chemistry
On-line version ISSN 1996-840X
IDAHOSA, Kenudl C. et al. Elucidation of the complex Baylis-Hillman reaction of 3-methoxy-2-nitrobenzaldehyde with methyl vinyl ketone. S.Afr.j.chem. (Online) [online]. 2011, vol.64, pp. 144-150. ISSN 1996-840X.
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 distribution in this complex reaction.
Keywords : Baylis-Hillman reaction; mechanism; kinetics; 1H NMR spectroscopic analysis; bis-(MVK)Baylis-Hillman products.