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Synlett 2012(2): 239-242  
DOI: 10.1055/s-0031-1290121
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

α-Formylation of α-Substituted Ketones

Jamal Hassan, Christopher J. Richards*
School of Chemistry, University of East Anglia, Norwich, NR4 7TJ, UK
Fax: +44(1603)592003; e-Mail: Chris.Richards@uea.ac.uk;
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Publication History

Received 1 November 2011
Publication Date:
22 December 2011 (online)

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Abstract

The reaction of (chloromethylene)dimethylammonium chloride (generated in situ from oxalyl chloride and DMF) with α-substituted ketones in CH2Cl2, followed by workup with aqueous NaHCO3, gave β-keto aldehydes containing an α-quaternary centre (8-88% yield).

Key words

aldehydes - enols - hydrolysis - ketones - tautomerism

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