1574666-21-9Relevant academic research and scientific papers
Oxidation of alcohols and activated alkanes with lewis acid-activated tempo
Nguyen, Thuy-Ai D.,Wright, Ashley M.,Page, Joshua S.,Wu, Guang,Hayton, Trevor W.
, p. 11377 - 11387 (2014)
The reactivity of MCl3(η1O) (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(η1OH) (23) and [FeBr2(η1OH)]2(μ-O) (24), via oxidation of the solvent, Et2O.
