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Application of the anionic homologous Fries-rearrangement to the synthesis of 3-alkylbenzofuran-2(3H)-ones

Azzena, Ugo Gavino and Pisano, Luisa and Pittalis, Mario (2008) Application of the anionic homologous Fries-rearrangement to the synthesis of 3-alkylbenzofuran-2(3H)-ones. Applied Organometallic Chemistry, Vol. 22 (9), p. 523-528. eISSN 1099-0739. Article.

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DOI: 10.1002/aoc.1437


We have developed an effective organometallic-based procedure allowing the employment of 2-methylphenols as easily available starting materials in the synthesis of 3-alkylbenzofuran-2(3H)-ones. The first step of this protocol, an anionic homologous Fries-rearrangement, afforded 2-(2-tert-butyldimethylsilyloxyaryl)acetamides, which were selectively metalated and monoalkylated at the benzylic position. Acidic work-up of crude products afforded the desired heterocycles in satisfactory overall yields.

Item Type:Article
ID Code:1793
Uncontrolled Keywords:Alkylation, benzofuran-2(3H)-ones, Fries rearrangement, metalation, organolithiums, regioselectivity
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Additional Information:Pubblicato online il 28 luglio 2008.
Deposited On:18 Aug 2009 10:06

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