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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
Author(s) -
Canévet JeanClaude,
Graff Yves
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620527
Subject(s) - chemistry , friedel–crafts reaction , aryl , medicinal chemistry , carbocation , sulfuric acid , derivative (finance) , tetrahydrofuran , aluminium chloride , chloride , triflic acid , stereochemistry , organic chemistry , catalysis , aluminium , alkyl , solvent , financial economics , economics
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.