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 (free Supporting Information)
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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