RESEARCH ARTICLE

 

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

 

 

Kenudl C. Idahosa; Duduzille M. Molefe; Vusumzl E. Pakade; Michael E. Brown ; Perry T. Kaye^*

Department of Chemistry and Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown, 6140, South Africa

 

 

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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. 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

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Full text available only in pdf format.

 

Acknowledgements

The authors thank the South African Medical Research Council (MRC) for a bursary (D.M.M.), the MRC and Rhodes University for generous financial support and Dr P. Kempgens and A. Soper for assistance with NMR spectroscopy.

 

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Received 17 June 2011
Revised 24 September 2011
Accepted 26 September 2011

 

 

Submitted by invitation to celebrate 2011 the 'International Year of Chemistry'.
* To whom correspondence should be addressed. E-mail: p.kaye@ru.ac.za