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2011•South African Journal of ChemistryOpen access

Elucidation of the complex Baylis-Hillman reaction of 3-methoxy-2-nitrobenzaldehyde with methyl vinyl ketone

Kenudl C. Idahosa, Duduzille M. Molefe, Vusumzi Emmanuel Pakade, Michael E. Brown, Perry T. Kaye

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Abstract

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.  1 H 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, 1 H NMR spectroscopic analysis, bis-(MVK)Baylis-Hillman products

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What this paper is about

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.  1 H 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, 1 H NMR spectroscopic analysis, bis-(MVK)Baylis-Hillman products

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Available abstract

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.  1 H 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, 1 H NMR spectroscopic analysis, bis-(MVK)Baylis-Hillman products

Key concepts: Methyl vinyl ketone, Chemistry, DABCO, Baylis–Hillman reaction, Adduct, Diastereomer, Ketone, Nuclear magnetic resonance spectroscopy

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