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ChemInform Abstract: Synthesis and Reactions of Some Dinitrodiazoquinones.

✍ Scribed by Jan Bergman; Thomas Brimert

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199934115

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✦ Synopsis

Synthesis and Reactions of Some Dinitrodiazoquinones.

-Nitration of simple anilines in the system nitric acid-sulfuric acid affords novel p-diazoquinones [cf. (II)] in moderate to good yields. The reaction is proposed to go via an N,3,4,5-tetranitroaniline, which can be trapped as its O-methylnitramine (IX)/(X), and which undergoes a nitro-nitrito rearrangement to furnish the diazoquinone. Reaction of diazoquinone (II) with strong acids, with reductant H 3 PO 2 and under Staudinger conditions is studied. The previously proposed formation of an o-diazoquinone (XII) by nitration of o-methylaniline (XI) is confirmed.

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