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Synlett 1991; 1991(7): 493-496
DOI: 10.1055/s-1991-20774
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New [1,4] Sigmatropic Rearrangement of Ammonium Benzylides: Synthesis of ortho-Cyanomethyl-Substituted Aromatic Aldehydes

Andrzej Jończyk* , Dariusz Lipiak, Krzysztof Sienkiewicz
  • *Department of Chemistry, Technical Univesity (Politechnika), Koszykowa 75, PL-00-662 Warsaw, Poland
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Publication Date:
07 March 2002 (online)

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The treatment of (arylcyanomethyl)(cyanomethyl)dimethylammonium salts 3 with base/solvent systems A (25 % aq sodium hydroxide/benzene), B (solid potassium carbonate/dimethylformamide or C (25 % aq ammonia/dichloromethane) generated ylides which undergo [3,2] and/or a new [1,4] sigmatropic rearrangement to give ortho-cyanomethyl-substituted 2-dimethylamino-2-phenylacetonitriles 5 and/or 6. The unmasking of the carbonyl group in these products gave ortho-cyanomethyl-substituted aromatic aldehydes 7 and/or 8, respectively.