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Synthesis 2005(10): 1611-1618  
DOI: 10.1055/s-2005-865296
PAPER
© Georg Thieme Verlag Stuttgart · New York

A General Synthesis of Quinone Ammonium Salts

David Wiedenfeld*a, Mark A. Mintona, David R. Glassa, Vladimir N. Nesterova, Kila D. Nsamenanga, Dong Hanb
a Department of Natural Sciences - Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, USA
Fax: +1(505)4543202; e-Mail: dwiedenfeld@nmhu.edu;
b Department of Chemistry, University of North Texas, Denton, TX 76205, USA
Further Information

Publication History

Received 17 December 2004
Publication Date:
07 April 2005 (online)

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Abstract

A three-step procedure has been developed to convert substituted p-dimethoxybenzenes to quinone ammonium salts. Five examples of quinone ammonium salts have been prepared with this procedure. In the first step, the aromatic species is reacted with N-(hydroxymethyl)trifluoroacetamide and trifluoroacetic acid. The trifluoroacetamide product is then oxidatively demethylated and finally hydrolyzed to afford the quinone ammonium salt.

Key words

ammonium quinones - dimerizations - electrophilic aromatic substitutions - crystal structures - ammonium salts

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1

Current address: Department of Medicinal Chemistry, Genomics Institute of the Novartis Research Foundation, 10675 John Jay Hopkins Drive, San Diego, CA 92121.

12

Chlorinated precursors for amidomethylation were prepared by addition [13] of anhydrous hydrogen chloride [14] to the three isomers of dimethyl-1,4-benzoquinone (xyloquinones) followed by O-methylation with dimethyl sulfate under phase transfer conditions. [15] The bromo substrate was prepared by direct bromination of the hydroquinone dimethyl ether. The cyano derivative was prepared by cyanide displacement [9] of the bromide.