Tag: M.W=300-350

Lambert, Kyle M. published the artcileFacile Oxidation of Primary Amines to Nitriles Using an Oxoammonium Salt, Computed Properties of 219543-09-6, the publication is Organic Letters (2014), 16(24), 6484-6487, database is CAplus and MEDLINE.

The oxidation of primary amines using a stoichiometric quantity of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in CH₂Cl₂-pyridine solvent at room temperature or at gentle reflux affords nitriles in good yield under mild conditions. The mechanism of the oxidation, which has been investigated computationally, involves a hydride transfer from the amine to the oxygen atom of 1 as the rate-limiting step.

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, Computed Properties of 219543-09-6.

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

Merbouh, Nabyl published the artcilePreparation of tetramethylpiperidine-1-oxoammonium salts and their use as oxidants in organic chemistry. A review, SDS of cas: 219543-09-6, the publication is Organic Preparations and Procedures International (2004), 36(1), 3-31, database is CAplus.

A review. The discovery of 2,2,6,6-tetramethylpiperidine-based oxoammonium salts (I; R = oxo, H, OH, NH₂, NHAc, OMe, OBz) in 1965 by Golubev et al has led to the synthesis of a number of oxoammonium-based oxidizing agents with diverse properties. However, many of the oxoammonium salts or their precursors are either not com. available or are expensive. Reports of their preparation are spread over 40 yr of literature. This review is a compilation of the most often cited and most practical procedures for their syntheses and includes exptl. details. A large body of work detailing the use of oxoammonium salts as catalytic and stoichiometric oxidants in preparative organic chem. also accumulated over the past four decades. The review of their use, however, will focus on the literature from 1990 to date, excluding the patent literature, as a number of excellent earlier reviews on select aspects of this chem. are available. The goal of this review is to allow organic chemists to prepare and study oxoammonium salts, irresp. of their list prices or com. availability. Oxoammonium salts I are derived from nitroxide free radicals (II) by a one-electron oxidation Nitroxides are generally prepared by oxidation of the corresponding amine 2,2,6,6-tetramethylpiperidine derivatives (III). The α-Me groups are crucial for the stabilization of the oxoammonium salts. A number of 4-substituted tetramethylpiperidine derivatives were used for the synthesis of oxoammonium salts, combined with several counter ions. Oxoammonium salts are potent but selective oxidants. They can either be prepared in situ from a nitroxide by reaction with a secondary oxidant, thus making the nitroxide a catalyst, or they can be used as stoichiometric oxidants. They are versatile oxidants in organic chem. and the mild, transition metal-free reaction conditions and the selectivity of the oxidations recommend these oxidants for wider use. Further, the option for tandem reactions will greatly increase the utility of these reagents.

Organic Preparations and Procedures International 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, SDS of cas: 219543-09-6.

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

Merbouh, Nabyl published the artcileOxoammonium salts. Part 8: Oxidations in base: oxidation of O-1 unprotected monosaccharides to lactones using 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate, HPLC of Formula: 219543-09-6, the publication is Tetrahedron Letters (2001), 42(50), 8793-8796, database is CAplus.

The oxidant, 4-acetylamino-2,2,6,6-tetramethylpiperidine-oxoammonium tetrafluoroborate in pyridine/CH₂Cl₂, is reported to be an excellent reagent for the conversion of hemiacetals to lactones. Specifically, the conversion of 1-O unprotected sugars to their corresponding aldonolactones is achieved in high yields. The basic reaction conditions partially overcome some disadvantages reported for oxoammonium-type oxidants, namely the inability to run the reaction in the presence of acid-labile groups and in the presence of β-oxygens.

Tetrahedron 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, HPLC of Formula: 219543-09-6.

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

Miller, Shelli A. published the artcileOxidation of terminal diols using an oxoammonium salt: a systematic study, Formula: C11H21BF4N2O2, the publication is Organic & Biomolecular Chemistry (2017), 15(13), 2817-2822, database is CAplus and MEDLINE.

A systematic study of the oxidation of a range of terminal diols is reported, employing the oxoammonium salt 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO⁺ BF₄^–) as the oxidant. For substrates bearing a hydrocarbon chain of seven carbon atoms or more, the sole product is the dialdehyde. A series of post-oxidation reactions have been performed showing that the product mixture resulting from the oxidation step can be taken on directly to a subsequent transformation. For diols containing four to six carbon atoms, the lactone product is the major product upon oxidation In the case of 1,2-ethanediol and 1,3-propanediol, when using a 1 : 0.5 stoichiometric ratio of substrate to oxidant, the corresponding monoaldehyde is formed which reacts rapidly with further diol to yield the acetal product. This is of particular synthetic value given both the difficulty of their preparation using other approaches and also their potential application in further reaction chem.

Organic & Biomolecular 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, Formula: C11H21BF4N2O2.

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

Pradhan, Priya P. published the artcileOxidative Cleavage of Benzylic and Related Ethers, Using an Oxoammonium Salt, Synthetic Route of 219543-09-6, the publication is Journal of Organic Chemistry (2009), 74(24), 9524-9527, database is CAplus and MEDLINE.

Benzylic ethers and related ArCH₂OR substrates are oxidatively cleaved by 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (I) in wet CH₃CN at room temperature to give the corresponding aromatic aldehyde and alc. in high yield. Primary or secondary alc. products are further oxidized by I to give carboxylic acids and ketones, resp. The oxidation likely involves a formal hydride abstraction from the benzylic carbon as evidenced by slow reaction of substrates bearing electron-withdrawing substituents.

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, Synthetic Route of 219543-09-6.

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

Pradhan, Priya P. published the artcileEne-like addition of an oxoammonium cation to alkenes: highly selective route to allylic alkoxyamines, SDS of cas: 219543-09-6, the publication is Organic Letters (2006), 8(24), 5485-5487, database is CAplus and MEDLINE.

The addition of oxoammonium cation of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in an ene-like fashion to trisubstituted alkenes afforded allylic alkoxyamines, e.g., I, in high yields.

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, SDS of cas: 219543-09-6.

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

Tilley, Leon J. published the artcileA revised preparation of (4-acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and 4-acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate: reagents for stoichiometric oxidations of alcohols, Quality Control of 219543-09-6, the publication is Synthesis (2013), 45(3), 326-329, database is CAplus.

Revised preparations of (4-acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and the corresponding oxoammonium salt, 4-acetamido-2,2,6,6-tetramethyl-1-oxoammonium tetrafluoroborate, are presented together with some of the important properties of these two oxidizing reagents.

Synthesis 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 C8H16O2, Quality Control of 219543-09-6.

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

Carlet, Federica published the artcileOxoammonium-Mediated Allylsilane-Ether Coupling Reaction, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is European Journal of Organic Chemistry (2021), 2021(15), 2162-2168, database is CAplus.

A new C(sp³)-H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- Me ethers has been developed. The C-C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

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, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Gorski, Bartosz published the artcileCopper-catalysed amination of alkyl iodides enabled by halogen-atom transfer, Synthetic Route of 170364-89-3, the publication is Nature Catalysis (2021), 4(7), 623-630, database is CAplus.

Here, an alternative amination strategy was demonstrated for the synthesis of alkyl amines, e.g., I where alkyl iodides are used as radical precursors instead of electrophiles. Use of α-aminoalkyl radicals enabled the efficient conversion of the iodides into the corresponding alkyl radical by halogen-atom transfer, while copper catalysis assembled the sp³ C-N bonds at room temperature The process provided SN²-like programmability, and application in late-stage functionalization of several densely functionalized pharmaceuticals demonstrated its utility in the preparation of valuable N-alkylated drug analogs.

Nature Catalysis published new progress about 170364-89-3. 170364-89-3 belongs to piperidines, auxiliary class Indole,Piperidine,Amide, name is tert-Butyl 4-(1H-indol-1-yl)piperidine-1-carboxylate, and the molecular formula is C18H24N2O2, Synthetic Route of 170364-89-3.

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

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