Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenyl­carboxaldehydes

Hee Nam Lim; Sang-Hoon Ji; Kee-Jung Lee

doi:10.1055/s-2007-983812

PAPER

Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenylcarboxaldehydes

Hee Nam Lim, Sang-Hoon Ji, Kee-Jung Lee*
Organic Synthesis Laboratory, Department of Chemical Engineering, Hanyang University, Seoul 133-791, South Korea
Fax: +82(2)22984101; e-Mail: leekj@hanyang.ac.kr;

Abstract

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Abstract

Treatment of propiolic acid esters or N,N-dimethylpropynamide and various 2-biphenylcarboxaldehydes with tetrabutylammonium iodide/zirconium(IV) chloride, titanium(IV) chloride/dimethyl sulfide, or titanium(IV) bromide/dimethyl sulfide or treatment of methyl acrylate and 2-biphenylcarboxaldehydes with 1,4-diazabicyclo[2.2.2]octane (DABCO) and triethanolamine induce an aldol-type reaction to furnish β-halo-α-(hydroxymethyl)acrylates or α-(hydroxymethyl)acrylates, respectively. These can be used for the preparation of 2-(9H-fluoren-9-yl)acrylic acid derivatives by intramolecular Friedel-Crafts reaction with sulfuric acid in tetrachloromethane.

Key words

Morita-Baylis-Hillman reaction - Friedel-Crafts reaction - 2-(9-fluorenyl)acrylic acid derivative - 2-biphenylcarboxaldehyde - sulfuric acid

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Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenyl­carboxaldehydes

Synthesis of 2-(9-Fluorenyl)acrylic Acid Derivatives via Intramolecular Friedel-Crafts Reaction of Morita-Baylis-Hillman Adducts of 2-Biphenylcarboxaldehydes