Mandelic Acid as Synthetic Equivalent of Benzoyl Carbanion. Synthesis of Nitrobenzophenones

Gonzalo Blay; Luz Cardona; Isabel Fernández; Raquel Michelena; José R. Pedro; Teresa Ramírez; Rafael Ruiz-García

doi:10.1055/s-2003-42123

LETTER

Mandelic Acid as Synthetic Equivalent of Benzoyl Carbanion. Synthesis of Nitrobenzophenones

Gonzalo Blay, Luz Cardona, Isabel Fernández, Raquel Michelena, José R. Pedro*, Teresa Ramírez, Rafael Ruiz-García
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot (València), Spain
Fax: +34(96)3544328; e-Mail: jose.r.pedro@uv.es.;

Abstract

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Abstract

Nitrobenzophenones are prepared from a mandelic acid dioxolanone. The sequence starts with the aromatic nucleophilic substitution of the enolate of the dioxolanone onto p-fluoronitrobenzenes, followed by hydrolysis of the acetal moiety and oxidative decarboxylation of the resulting α-hydroxyacids. The whole sequence involves the use of mandelic acid as synthetic equivalent of the benzoyl carbanion.

Key words

acetals - nucleophilic aromatic substitutions - ketones - oxygen - oxidations - decarboxylation

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References

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