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Réactions de Friedel et Crafts de dérivés aromatiques sur les composés dioxo-1,4,2,3-non saturés. IV. Réactions des hydroxy-5-ouchloro-5-diméthyl-3,5- ou diméthyl-4,5-dihydro-2,5-furannones-2

✍ Scribed by Jean-Claude Canévet; Yves Graff

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
454 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Friedel‐Crafts reactions of aromatic derivatives with 1,4‐dicarbonyls 2,3‐éthylenic compounds. Part IV. Reactions of 5‐hydroxy or 5‐chloro 3,5‐dimethyl or 4,5‐dimethyl 2 (5 H) furanones

We studied the Friedel‐Crafts reactions of 2‐(5__H__)‐furanones. In the presence of sulfuric acid and of an aromatic derivative, 5‐hydroxy‐ or 5‐chloro‐5‐methyl‐2‐(5__H__)‐furanones with one methyl group either in the 3 position, or in the 4 position generally give the corresponding 5‐aryl‐2‐(5__H__)‐furanones, while with aluminium chloride, it is possible to obtain, when a reaction takes place, isomeric 1__H__‐indenecarboxylic acids. However, in a particular case, an addition to the substrate's double bond is observed. The 3‐aryl‐5‐hydroxy‐tetrahydrofuran‐2‐one obtained is methylated in two ways and gives either a cyclic product, or a linear one. In two cases tautomerism between 1__H__‐1‐indenecarboxylic acid and 1__H__‐3‐indenecarboxylic has been shown by ^1^H‐NMR.

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