The Journal of Organic Chemistry

Hydroxylation of nitroarenes with alkyl hydroperoxide anions via vicarious nucleophilic substitution of hydrogen

M Makosza, K Sienkiewicz

Index: Makosza, Mieczyslaw; Sienkiewicz, Krzysztof Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4199 - 4208

Full Text: HTML

Citation Number: 61

Abstract

Carbo-and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o-and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this ...

 Related Synthetic Route

~79%

~78%

~76%

~23%

~84%

~18%

~83%

~11%

~66%

~65%

~63%

~86%

~88%

~51%

~78%

~86%

~83%

~89%

~27%

~80%