58810-39-2Relevant articles and documents
Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles
Driver, Tom G.,Sung, Siyoung,Wink, Donald J.,Zadrozny, Joseph M.,Zhao, Yingwei,Zhu, Haoran
supporting information, p. 19207 - 19213 (2021/08/09)
tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.
Studies on tertiary amine oxides. LXXI. Some electrophilic reactions of 1-hydroxy-2-phenylindole
Nagayoshi,Saeki,Hamana
, p. 1827 - 1831 (2007/10/02)
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