Table 6.

Flow hydrodediazoniation of aromatic amines.

Starting material (1.0 mmol) in THF (10 mL), iso-pentyl nitrite (1.2 mmol) in THF (10 mL), 10 mL coil volume, 20 min residence time. ^a 20 mL of THF was used for both reagent solutions. ^b DMF (2 mL) was added to the starting material solution to improve solubility. ^c Concentrations of 0.5 mmol of starting material and 0.6 mmol of isopentyl nitrite. ^d Concentrations of 10.0 mmol of starting material and 12.0 mmol of isopentyl nitrite. Yield refers to pure, isolated and characterised yield. Detected refers to the conversion of starting material to product as quantified by integration of product ¹H-NMR peaks relative to a quantified internal standard of nitrobenzene. No reaction refers to compounds for which there was no evidence of formation and only starting material was recovered.