Arynic condensation of ketone enolates—XIV: Condensation of aromatic α,β-unsaturated ketone enolates on arynes |
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Authors: | M Essiz G Guillaumet P Caubere |
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Institution: | Laboratoire de Chimie Organique I, ERA CNRS No. 476, Université de Nancy I Case Officielle 140, 54037 Nancy Cédex, France |
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Abstract: | Benzyne and 1-naphthyne (generated from the corresponding halogeno derivatives and the Complex Base NaNH2-ButONa) condense with α,β-unsaturated ketone enolates β-substituted by an aromatic ring and only enolisable in the α'-position, to lead to α-tetralones and/or indanones. The reaction path depends upon the nature of the ketone enolate and, less strongly, on the solvent. The reaction mechanism is discussed. These reactions constitute new simple and efficient syntheses of numerous α-tetralones and indanones. |
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