Synthesis of polynitrobenzenes. Oxidation of polynitroanilines and their N-hydroxy, N-methoxy, and N-acetyl derivatives

…, AT Nielsen, C Bergens, WS Wilson

Index: Atkins, Ronald L.; Nielsen, Arnold T.; Bergens, Cynthia; Wilson, William S. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 503 - 507

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Citation Number: 19

Abstract

Nitro-substituted arylhydroxylamines and alkoxyamines have been oxidized to polynitroaryl compounds by utilizing ozone. Polynitroanilines have been oxidized to polynitroaromatics by peroxydisulfuric acid generated in situ from SO3 and ozone. Thus N-hydroxy-2, 4, 6- trinitroaniline (la) or N-methoxy-2, 4, 6-trinitroaniline (lb) was cleanly oxidized to 1, 2, 3, 5- tetranitrobenzene (2) by reaction with ozone in methylene chloride. Weakly basic amines ...

~99%

~61%

~94%

~40%

~93%

~95%

~98%

~99%

~29%

~32%

~50%

~31%

~52%

~5%

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