Aniline → 1-Phenoxy-2,2,6,6-tetramethylpiperidine

Participants

Reaction Steps

To a suspension of 3.9 g (25 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidine, 11.76 g (114 mmol) of tert-butyl nitrite and 25 mg (0.25 mmol) of copper(II) fluoride in 120 mL of acetonitrile at 65° C. under a nitrogen atmosphere is added dropwise over 30 minutes 6.98 g (75 mmol) of aniline. The evolution of gas is observed during the addition of the aniline. The dark red reaction mixture is kept at 65° C. for an additional ten minutes followed by cooling to ambient temperature. The reaction mixture is then concentrated to a thick oil which turns into a semi-solid upon standing. The residue is purified by vacuum flash chromatography (heptane) to give 4.3 g of a colorless oil in 74.1% yield based on nitroxyl. The structure is confirmed by 1Hnmr analysis, mass spectroscopy and elemental analyses.

Provenance & Evidence