Hydroxylation of nitro-(pentafluorosulfanyl)benzenes via vicarious nucleophilic substitution of hydrogen

Para- and meta-nitro-(pentafluorosulfanyl)benzenes react with anions of cumyl hydroperoxide in the presence of t-BuOK in liquid ammonia to form nitro-(pentafluorosulfanyl)phenols. Their reduction with hydrogen in the presence of Raney-Nickel provides amino-(pentafluorosulfanyl)phenols. (C) 2011 Elsevier Ltd. All rights reserved.