57309-24-7

Upstream product

• 1969-74-0 2-phenylisatogen 
• 18648-69-6 (2-(2-nitrophenyl)ethene-1,1-diyl)dibenzene 
• 552-89-6 2-nitro-benzaldehyde 
• 253684-24-1 1-(2,2-dibromovinyl)-2-nitrobenzene 

Downstream Products

• 65817-75-6 1-oxy-2,2-diphenyl-2H-indole-3,7-dione 
• 83195-93-1 1-Oxy-2,2-diphenyl-2H-indole-3,5-dione 
• 85036-16-4 5-tert-Butoxy-1-oxy-2,2-diphenyl-2H-indole-3,7-dione 
• 85036-19-7 7-tert-Butoxy-1-oxy-2,2-diphenyl-2H-indole-3,5-dione 
• 75654-78-3 5-tert-Butoxy-2,2-diphenyl-1,2-dihydro-indol-3-one 
• 81235-53-2 7-tert-Butoxy-2,2-diphenyl-1,2-dihydro-indol-3-one 
• 85036-23-3 1-Methoxy-2,2-diphenyl-1,2-dihydro-indol-3-one 
• 57309-29-2 1,2-dihydro-2,2-diphenyl-3H-indole-3-one-1-oxyl 

Relevant academic research and scientific papers

Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles

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.