A General Synthesis of Quinone Ammonium Salts

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

References

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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.