Bobbitt, James M.’s team published research in Journal of Organic Chemistry in 79 | CAS: 219543-09-6

Journal of Organic Chemistry 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.

Bobbitt, James M. published the artcileOxoammonium Salt Oxidations of Alcohols in the Presence of Pyridine Bases, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Organic Chemistry (2014), 79(3), 1055-1067, database is CAplus and MEDLINE.

Oxidations of alcs. containing a β-oxygen atom with the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in the presence of pyridine yielded dimeric esters, while in the presence of 2,6-lutidine the oxidations yielded aldehydes. The changes in oxidation reactivity with the steric hindrance of the pyridine catalyst are explained by formation of betaines between unhindered pyridines and aldehydes which undergo oxidation to acylpyridinium ions followed by substitution reactions with the starting alcs. to yield esters; hindered pyridines do not form betaines with aldehydes and so do not react further. Six alcs. containing β-oxygen substituents were oxidized chemoselectively to aldehydes in the presence of 2,6-lutidine. The relative reactivities of a set of alcs. toward oxoammonium ion-mediated oxidation was determined An overall mechanism for oxoammonium cation oxidations is suggested based on the premise that nucleophilic additions to the oxoammonium ions occur by addition to the oxygen atom of the pos. charged nitrogen-oxygen double bond; possible mechanisms for oxidations of β-alkoxy alcs. to aldehydes and esters are given. Transition state structures and free energies of transition states and products were calculated for two of three potential mechanisms.

Journal of Organic Chemistry 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