Methyl Hydrazinocarboxylate as a Practical Alternative to Hydrazine in the Wolff-Kishner Reaction

Philippa B. Cranwell*, Andrew T. Russell*, Christopher D. Smith*

*Department of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AD, UK, Email: p.b.cranwellreading.ac.uk, a.t.russellreading.ac.uk, c.d.smithreading.ac.uk

P. B. Cranwell, A. T. Russell, C. D. Smith, Synlett, 2016, 27, 131-135.

DOI: 10.1055/s-0035-1560805

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Abstract

A facile protocol for the reduction of aromatic ketones and aldehydes to the corresponding methylene unit involves the synthesis of a carbomethoxyhydrazone intermediate that is easily decomposed to the reduced product. The reaction avoids the use of pernicious hydrazine.

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Key Words

reduction, aldehydes, ketones, heterocycles, hydrazones, hydrazine, alkanes, Wolff-Kishner Reduction

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ID: J60-Y2016