Reactions of 1,3-Diaryl-2-chloropropane-1,3-diones with Nucleophiles − Cyanide-Induced Retro-Claisen−Claisen Condensation

Treatment of some 1,3‐diaryl‐2‐chloropropane‐1,3‐diones, acyclic chloro‐substituted enaminones and β‐oxo esters with nucleophiles was shown to proceed easily with the formation, at least in the first stage, of formal nucleophilic substitution products. Treatment of enaminones and β‐oxo esters with a...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-04, Vol.2004 (8), p.1765-1773
Main Authors: Roshchupkina, Galina I., Gatilov, Yury V., Rybalova, Tatyana V., Reznikov, Vladimir A.
Format: Article
Language:English
Subjects:
Diaroylmethanes
Enaminones
Ketones
Nucleophilic substitution
Retro-Claisen−Claisen condensation
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Summary:Treatment of some 1,3‐diaryl‐2‐chloropropane‐1,3‐diones, acyclic chloro‐substituted enaminones and β‐oxo esters with nucleophiles was shown to proceed easily with the formation, at least in the first stage, of formal nucleophilic substitution products. Treatment of enaminones and β‐oxo esters with azide and cyanide ions proceeds with the preservation of the skeleton, whereas chloro‐substituted diaroylmethanes undergo retro‐Claisen−Claisen condensation reactions in the course of the reaction with cyanide. Dibenzoylchloromethane reacts with azide and cyanide ions with fragmentation of the molecule and subsequent reassembly, resulting in benzoylated benzaldehyde cyanohydrin and a 1,3‐oxathiol derivative, respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300739