Elsevier

Tetrahedron

Volume 34, Issue 13, 1978, Pages 1935-1942
Tetrahedron

Réactions de friedel-crafts de dérivés aromatiques sur des composés dicarbonylés-1,4éthyléniques-2,3.ii alkylations par quelques hydroxy-5 ou chloro-5 dihydro-2,5 furannones-2. nouvelle méthode de synthèse des acides 1h-indènecarboxyliques-1

https://doi.org/10.1016/0040-4020(78)80100-8Get rights and content

Résumé

En présence de catalyseurs acides, les diméthyl-3,4 hydroxy-5, ou chloro-5, dihydro-2,5 furannones-2 diversement substituées en position 5 réagissent avec les dérivés aromatiques pour donner, dans un premier temps, les aryl-5 diméthyl-3,4 dihydro-2,5 furannones-2 correspondantes. Certaines de ces aryl-5 furannones sont susceptibles de s'isomériser en acides 1H-indènecarboxyliques par ouverture du cycle, transposition de type allylique et alkylation intramoléculaire. La nature du catalyseur est importante: l'acide sulfurique permet de s'arrêter au stade des aryl-5 furannones tandis que le chlorure d'aluminium peut conduire directement aux acides indéniques. Ce type de réactions est assez général; des mécanismes réactionnels sont proposés et discutés.

Abstract

With acid catalysts, 3,4-dimethyl-5-hydroxy (or 5-chloro)-2-(5H)furanones substituted at position 5, react with aromatic derivatives to give the corresponding 5-aryl-3,4-dimethyl-2(5H)-furanones in a first step. Some of these 5-aryl furanones are able to isomerize into 1H-indenecarboxylic acids by ring-opening, allylic-type-transposition, and intramolecular alkylation. The nature of the catalyst is important: sulfuric acid leads to the 5-aryl furanones, while aluminium chloride leads in one step, to indenecarboxylic acids. This type of reaction is fairiy general. Reaction mechanisms are proposed and discussed.

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