Download PDF
Synlett 1991; 1991(7): 493-496
DOI: 10.1055/s-1991-20774
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >