115772-99-1Relevant academic research and scientific papers
Dehydrogenation of perfluoroalkyl ketones by using a recyclable oxoammonium salt
Hamlin, Trevor A.,Kelly, Christopher B.,Leadbeater, Nicholas E.
supporting information, p. 3658 - 3661 (2013/07/19)
A novel dehydrogenation reaction of perfluoroalkyl ketones by the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO+BF4-, Bobbitt's salt, 1) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1a), can easily be recovered and used to regenerate the oxoammonium salt. The dehydrogenation of perfluoroalkyl ketones by using an oxoammonium salt is reported. The reaction proceeds under mildly basic conditions and affords α,β-unsaturated products in fair to excellent yields. The reaction likely proceeds through a two-step sequence. The spent oxidant can easily be recovered and used to regenerate the oxoammonium salt. Copyright
