Tag: M.W=300-350

Kaetzel, Nathaniel D. published the artcileOxidation of aldehydes to nitriles with an oxoammonium salt: preparation of piperonylonitrile, Related Products of piperidines, the publication is Organic Syntheses (2020), 294-313, database is CAplus.

The detailed one-step preparation of piperonylonitrile via oxidation of piperonal with Bobbitt’s oxoammonium salt using hexamethyldisilazane as nitrogen source was reported. Application of the methodol. to the synthesis of other nitriles, as well as the use of oxoammonium salts in other oxidative transformations, was also discussed.

Organic Syntheses 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, Related Products of piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Kashparova, V. P. published the artcileThe “one-pot” synthesis of 2,5-diformylfuran, a promising synthon for organic materials in the conversion of biomass, Quality Control of 219543-09-6, the publication is Russian Chemical Bulletin (2015), 64(5), 1069-1073, database is CAplus.

The organic ionic oxidant 4-acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate, [Pip*(O)][BF₄], was found to be compatible with both classical organic solvents and the ionic liquids [BMIm][Cl]/[BMIm][BF₄] (BMIm is 1-butyl-3-methylimidazolium), which are essential in the conversion of cellulose biomass. A unique NMR monitoring procedure developed in our group was used to study the conversion of fructose to 2,5-diformylfuran in ionic liquids This process can successfully be carried out in a “one-pot” fashion; [Pip*(O)][BF₄] efficiently oxidizes intermediate 5-hydroxymethylfurfural. The reaction is highly selective, giving 2,5-diformylfuran in 95% yield.

Russian Chemical Bulletin 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, Quality Control of 219543-09-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Biswas, Souvagya published the artcileEnantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis, COA of Formula: C11H21BF4N2O2, the publication is Angewandte Chemie, International Edition (2018), 57(2), 589-593, database is CAplus and MEDLINE.

Reported is the first enantioselective oxidative Pummerer-type transformation using phase-transfer catalysis to deliver enantioenriched sulfur-bearing heterocycles. This reaction includes the direct oxidation of sulfides to a thionium intermediate, followed by an asym. intramol. nucleophilic addition to form chiral cyclic N,S-acetals with moderate to high enantioselectivities. Deuterium-labeling experiments were performed to identify the stereodiscrimination step of this process. Further anal. of the reaction transition states, by multidimensional correlations and DFT calculations, highlight the existence of a set of weak noncovalent interactions between the catalyst and substrate that govern the enantioselectivity of the reaction.

Angewandte Chemie, International Edition 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, COA of Formula: C11H21BF4N2O2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Wertz, Sebastian published the artcileAmination of Benzoxazoles and 1,3,4-Oxadiazoles Using 2,2,6,6-Tetramethylpiperidine-N-oxoammonium Tetrafluoroborate as an Organic Oxidant, Category: piperidines, the publication is Angewandte Chemie, International Edition (2011), 50(48), 11511-11515, S11511/1-S11511/116, database is CAplus and MEDLINE.

No transition metals are necessary to convert benzoxazoles and 1,3,4-oxadiazoles into the corresponding pharmacol. interesting 2-aminated heterocycles by formal direct C(2)-amination using tetramethylpiperidine-N-oxoammonium tetrafluoroborate (TEMPO⁺BF₄^–) as an oxidant. Mechanistic studies were carried out, and the methodol. was also applied to the preparation of racemic MK-4305.

Angewandte Chemie, International Edition 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 C3H5BN2O2, Category: piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Ovian, John M. published the artcileAccessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic Letters (2017), 19(6), 1286-1289, database is CAplus and MEDLINE.

An operationally simple, robust, metal-free approach to the synthesis of N-acyl azoles from both alcs. and aldehydes is described. Oxidative amidation is facilitated by a com. available organic oxidant (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and proceeds under very mild conditions for an array of structurally diverse substrates. Tandem reactions of these activated amides, such as transamidation and esterification, enable further elaboration. Also, the spent oxidant can be recovered and used to regenerate the oxoammonium salt.

Organic Letters 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

Mercadante, Michael A. published the artcile1,3-γ-Silyl-elimination in electron-deficient cationic systems, Related Products of piperidines, the publication is Chemical Science (2014), 5(10), 3983-3994, database is CAplus.

Placement of an electron-withdrawing trifluoromethyl group (-CF₃) at a putative cationic center enhanced γ-silyl neighboring-group participation (NGP). In stark contrast to previously studied γ-silyl-substituted systems, the preferred reaction pathway was 1,3-γ-silyl elimination, giving ring closure over solvent substitution or alkene formation. The scope of this cyclopropanation reaction was explored for numerous cyclic and acyclic examples, proving this method to be a viable approach for preparing CF₃-substituted cyclopropanes and bicyclic systems, both containing quaternary centers. Rate-constants, kinetic isotope effects, and quantum mech. calculations provided evidence for this enhancement and further elaborated the disparity in the reaction outcome between these systems and previously studied γ-silyl systems.

Chemical Science 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, Related Products of piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

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

Lambert, Kyle M. published the artcileA Practical Oxidation Experiment for Undergraduate Students: Bobbitt′s Salt as a “Green” Alternative, Synthetic Route of 219543-09-6, the publication is Journal of Chemical Education, database is CAplus.

Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chem. courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chem. textbooks emphasize chromium-based oxidants that are no longer in regular use by practitioners, which may limit an instructor′s time to allocate to discussion of other oxidants. Further, laboratory courses have since either removed oxidation experiments or replaced them with oxidative processes not discussed in lectures, thus leading to a disconnect between the two learning settings. As part of an effort to bridge this divide and modernize the oxidation reactions discussed in our curricula, we have developed a new laboratory experiment that uses a com. available oxoammonium salt (Bobbitt′s salt) to cleanly oxidize cinnamyl alc. to cinnamaldehyde. In addition to being a safe, convenient, colorimetric and “green oxidant” suitable for use in the undergraduate teaching laboratory, the hydride-transfer mechanism allows for overlap with key course concepts presented in both introductory and advanced lecture courses. The procedure is well-suited for small and large organic I, II or advanced laboratory sections alike, and can be completed within a standard 3-4 h laboratory period. Aside from exposing students to a modern green oxidation protocol, the experiment contains expanded opportunities for interpretation of ¹H NMR, ¹³C NMR, and IR spectra. An optional addendum for advanced students involving Hammett correlations was also developed.

Journal of Chemical Education 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, Synthetic Route of 219543-09-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Hamlin, Trevor A. published the artcileToward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Organic Chemistry (2015), 80(16), 8150-8167, database is CAplus and MEDLINE.

A range of oxoammonium salt-based oxidation reactions have been explored computationally using d. functional theory (DFT), and the results have been correlated with exptl. derived trends in reactivity. Mechanistically, most reactions involve a formal hydride transfer from an activated C-H bond to the oxygen atom of the oxoammonium cation. Several new potential modes of reactivity have been uncovered and validated exptl.

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

Hamlin, Trevor A. published the artcileDehydrogenation of Perfluoroalkyl Ketones by Using a Recyclable Oxoammonium Salt, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is European Journal of Organic Chemistry (2013), 2013(18), 3658-3661, database is CAplus.

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) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. E.g., in presence of Bobbitt’s salt and 2,6-lutidine in refluxing CH₂Cl₂, dehydrogenation of PhCH₂CH₂COCF₃ gave 65% (E)-I. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy, can easily be recovered and used to regenerate the oxoammonium salt.

European 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