Dear All,
I was wondering if anyone used Bobbitt`s salt for alcohol oxidation. I have successfully oxidased my alcohol to carboxylic acid. My question is how do I regenerate Bobbitt`s salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-
oxoammonium tetrafluoroborate) so I can re-use it for another oxidation. Literature says it is possible, but as I`m not a chemist I would appreciate if someone could kindly explain it to me. Thank you very much.
Synthesis of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate and 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl and their use in oxidative reactions
Nature Protocols 8, 666–676 (2013) doi:10.1038/nprot.2013.028
Essentially, the paper shows that after the oxidation is complete you vacuum filter the reaction through a silica pad. The product is in the filtrate while the reduce Bobbitt's salt is in the precipitate. You wash the residue with water and reoxidise with H2O2. A possible problem I see is whether your acid product is soluble in DCM? If it is soluble you can follow this procedure, but if it is not soluble in DCM i.e. in the ppt with the salt then this procedure may need some tweaking.
you might also want to check out this link
http://orgsyn.org/demo.aspx?prep=v90p0215#ref9
section F Table 4 entry 2 shows a catalytic oxidation using the same reagent to carboxylic acid.
Maybe the following paper (Org. Lett., 2013, 15(9), 2222–2225) can help: http://pubs.acs.org/doi/abs/10.1021/ol400785d
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