Synthesis and reactions of trinitro-9,10-phenanthrenequinone derivatives

The reaction of 2,4,7-trinitro-9,10-phenanthrenequinone with CuCl in aqueous dimethylformamide or dimethyl sulfoxide at room temperature, followed by acidification, gave a stable red complex of 2,4,7-trinitro-9,10-dihydroxyphenanthrene with a solvent molecule. On heating in a polar aprotic solvent i...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 49; no. 7; pp. 1025 - 1030
Main Authors Andrievskii, A. M., Linko, R. V., Grachev, M. K.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.07.2013
Springer Nature
Subjects
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Review
Science & Technology
Phenanthrene
CuCl
Cyclic Sulfate
Nitro Group
Fluorenone
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Summary:The reaction of 2,4,7-trinitro-9,10-phenanthrenequinone with CuCl in aqueous dimethylformamide or dimethyl sulfoxide at room temperature, followed by acidification, gave a stable red complex of 2,4,7-trinitro-9,10-dihydroxyphenanthrene with a solvent molecule. On heating in a polar aprotic solvent in the presence of CuCl or other metal salt, 2,4,7-trinitro-9,10-phenanthrenequinone underwent benzilic acid rearrangement with formation of 2,4,7-trinitrofluorenone. The nitration of 9,10-sulfuryldioxyphenanthrene and subsequent decomposition of cyclic sulfates afforded previously unknown 1,3,6-trinitro- and 1,8-dinitro-9,10-phenanthrenequinones.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428013070117