Mercadante, Michael A. published the artcileSynthesis of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxammonium tetrafluoroborate and 4-acetamido-(2,2,6,6-tetramethyl-1-piperidinyl)oxyl and their use in oxidative reactions, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Nature Protocols (2013), 8(4), 666-676, database is CAplus and MEDLINE.
E authors describe the synthesis of a lesser-known stoichiometric oxidation reagent 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxammonium tetrafluoroborate [Bobbitt’s salt, 4-(acetylamino)-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate(1-)] (I) and 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (AcNH-TEMPO) (II). Several representative oxidation reactions are also presented to demonstrate the oxidative capability of Bobbitt’s salt. Bobbitt’s salt I has a range of applications, from the oxidation of various alcs. to their corresponding carbonyl derivatives to the oxidative cleavage of benzyl ethers, whereas II has been shown to serve as a catalytic or stoichiometric oxidant. The oxyl radical can be obtained in 85% yield over two steps on a one mol scale from com. available 4-amino-2,2,6,6-tetramethylpiperidine and is far more cost-effective to prepare inhouse than purchase com. An addnl. step converts the oxyl radical into the oxammonium salt (Bobbitt’s salt) I in 88% yield with an overall yield of 75%. The synthesis of the salt takes ∼5 d to complete. Oxammonium salts are metal-free, nontoxic and environmentally friendly oxidants (green chem. method). Preparation of I is also inherently a green process, as water can be used as a solvent and the use of environmentally unfriendly materials is minimized. Moreover, after it has been used, the spent oxidant can be recovered and used to regenerate I, thereby making the process recyclable. The synthesis of the target compound I was achieved by a reaction of 4-(Acetylamino)-2,2,6,6-tetramethyl-1-piperidinyloxy [(acetylamino)TEMPO]. Oxidation of 3-(4-methylphenyl)-2-propyn-1-ol provided 3-(4-methylphenyl)-2-propynoic acid. Oxidation of 1-decanol gave decanal.
Nature Protocols published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.
Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem