Details

Autor(en) / Beteiligte

• Nguyen, Thuy-Ai D
• Wright, Ashley M
• Page, Joshua S
• Wu, Guang
• Hayton, Trevor W

Titel

Oxidation of Alcohols and Activated Alkanes with Lewis Acid-Activated TEMPO

Ist Teil von

• Inorganic chemistry, 2014-11, Vol.53 (21), p.11377-11387

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2014

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The reactivity of MCl3(η1-TEMPO) (M = Fe, 1; Al, 2; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) with a variety of alcohols, including 3,4-dimethoxybenzyl alcohol, 1-phenyl-2-phenoxyethanol, and 1,2-diphenyl-2-methoxyethanol, was investigated using NMR spectroscopy and mass spectrometry. Complex 1 was effective in cleanly converting these substrates to the corresponding aldehyde or ketone. Complex 2 was also able to oxidize these substrates; however, in a few instances the products of overoxidation were also observed. Oxidation of activated alkanes, such as xanthene, by 1 or 2 suggests that the reactions proceed via an initial 1-electron concerted proton–electron transfer (CPET) event. Finally, reaction of TEMPO with FeBr3 in Et2O results in the formation of a mixture of FeBr3(η1-TEMPOH) (23) and [FeBr2(η1-TEMPOH)]2(μ-O) (24), via oxidation of the solvent, Et2O.