Tag: M.W=300-350

Richter, Heinrich published the artcileMild Metal-Free Tandem α-Alkylation/Cyclization of N-Benzyl Carbamates with Simple Olefins, Computed Properties of 219543-09-6, the publication is Angewandte Chemie, International Edition (2012), 51(34), 8656-8660, S8656/1-S8656/82, database is CAplus and MEDLINE.

Stereoselective synthesis of oxazines was achieved by metal-free tandem α-alkylation/cyclization of N-benzyl carbamates with olefins. E.g., in presence of TEMPO derivative (I) as oxidant, α-alkylation/cyclization of carbamate II (Ad = 1-adamantyl) gave a mixture of separable diastereomers 77% III and 16% IV.

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, Computed Properties of 219543-09-6.

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

Bobbitt, James M. published the artcileDiscussion addendum for: preparation of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1- oxoammonium tetrafluoroborate and the oxidation of geraniol to geranial (2,6-octadienal, 3,7-dimethyl-, (2e)-), Application In Synthesis of 219543-09-6, the publication is Organic Syntheses (2013), 215-228, database is CAplus.

A review. Addendum to an original article published by Bobbitt, J. M. and Merbouh, N. in Organic Synth. 2005, 82, 80. Revised preparations of I and II•BF₄^–, their solubility properties and relevance in stoichiometric alc. oxidation reactions, and examples of selective alc. oxidations of polyalcs. as well as other recent developments were 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, Application In Synthesis of 219543-09-6.

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

Bobbitt, James M. published the artcilePreparation of Some Homologous TEMPO Nitroxides and Oxoammonium Salts; Notes on the NMR Spectroscopy of Nitroxide Free Radicals; Observed Radical Nature of Oxoammonium Salt Solutions Containing Trace Amounts of Corresponding Nitroxides in an Equilibrium Relationship, Product Details of C11H21BF4N2O2, the publication is Journal of Organic Chemistry (2017), 82(18), 9279-9290, database is CAplus and MEDLINE.

Three new homologous TEMPO oxoammonium salts and three homologous nitroxide radicals have been prepared and characterized. The oxidation properties of the salts have been explored. The direct ¹³C NMR and EPR spectra of the nitroxide free radicals and the oxoammonium salts, along with TEMPO and its oxoammonium salt, have been successfully measured with little peak broadening of the NMR signals. In the spectra of all ten compounds (nitroxides and corresponding oxoammonium salts), the carbons in the 2,2,6,6-tetramethylpiperidine core do not appear, implying paramagnetic properties. This unpredicted overall paramagnetism in the oxoammonium salt solutions is explained by a redox equilibrium as shown between oxoammonium salts and trace amounts of corresponding nitroxide. This equilibrium is confirmed by electron interchange reactions between nitroxides with an N-acetyl substituent and oxoammonium salts with longer acyl side chains.

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, Product Details of C11H21BF4N2O2.

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

Borodkin, G. I. published the artcileReaction of Nitrosonium Tetrafluoroborate with Nitroxyl Radicals, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2003), 39(8), 1144-1150, database is CAplus.

It was established by means of multinuclear magnetic resonance method (¹H, ¹³C, ¹⁹F and ¹⁴N) that reaction of 2,2,6,6-tetramethyl-4-R-piperidin-1-oxyl radicals (R = H, OH, OMe, OCOPh, NHCOMe) with nitrosonium tetrafluoroborate gave rise to the corresponding 2,2,6,6-tetramethyl-1-oxo-4-R-piperidinium tetrafluoroborates. Linear correlations were found between the chem. shifts of atoms H⁴, C⁴ of cations and resp. σ₁-constants of substituents R and chem. shifts of C⁴ atom calculated from increments of substitution. The conformational features of the generated nitrosonium cations are considered on the grounds of vicinal coupling constants J_HH and quantum-chem. calculations by AM1 method.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) 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, Name: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Moon, Patrick J. published the artcileDecarboxylative Benzylation of Aryl and Alkenyl Boronic Esters, Recommanded Product: (3-(3-(Ethoxycarbonyl)piperidine-1-carbonyl)phenyl)boronic acid, the publication is Angewandte Chemie, International Edition (2018), 57(17), 4612-4616, database is CAplus and MEDLINE.

The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.

Angewandte Chemie, International Edition published new progress about 1218790-81-8. 1218790-81-8 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Ester,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (3-(3-(Ethoxycarbonyl)piperidine-1-carbonyl)phenyl)boronic acid, and the molecular formula is C15H20BNO5, Recommanded Product: (3-(3-(Ethoxycarbonyl)piperidine-1-carbonyl)phenyl)boronic acid.

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

Bailey, William F. published the artcileIntramolecular carbolithiation cascades as a route to a highly strained carbocyclic framework: competition between 5-exo-trig ring closure and proton transfer, Related Products of piperidines, the publication is Beilstein Journal of Organic Chemistry (2013), 537-543, database is CAplus and MEDLINE.

The preparation of fairly strained carbocyclic ring systems by intramol. 5-exo-trig ring closure has been well documented and the absence of proton transfers that would compromise such cyclizations is a hallmark of this chem. In an effort to explore the limitations of this approach to more highly strained systems, the preparation of a stellane (tricyclo[3.3.0.0^3,7]octane) framework by an intramol. carbolithiation cascade (tandem reaction) involving three coupled 5-exo-trig cyclization reactions of a vinyllithium group (I) derived from 2-bromo-4-vinyl-1,6-heptadiene by lithium-bromine exchange (substitution bromination) was investigated. The cascade does not afford 1-methylstellane. Rather, the cascade is terminated after two cyclizations by a proton transfer that occurs by an intermol. process catalyzed by trace amounts of endo-5-methyl-2-methylenebicyclo[2.2.1]heptane present in reaction mixtures as a consequence of inadvertent quenching of an intermediate alkyllithium during prolonged reaction times at room temperature The synthesis of the target compound I was achieved using 4-pentenoic acid 1,1-dimethylethyl ester as a starting material.

Beilstein 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, Related Products of piperidines.

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

Brenna, Elisabetta published the artcileChemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process, Category: piperidines, the publication is Advanced Synthesis & Catalysis (2018), 360(19), 3677-3686, database is CAplus.

A chemo-enzymic catalytic system, comprised of Bobbitt’s salt and laccase from Trametes versicolor, allowed the [1,3]-oxidative rearrangement of endocyclic allylic tertiary alcs. into the corresponding enones under an Oxygen atm. in aqueous media. The yields were in most cases quant., especially for the cyclopent-2-en-1-ol or the cyclohex-2-en-1-ol substrates without an electron withdrawing group (EWG) on the side chain. Transpositions of macrocyclic alkenols or tertiary alcs. bearing an EWG on the side chain were instead carried out in acetonitrile by using an immobilized laccase preparation Dehydro-Jasmone, dehydro-Hedione, dehydro-Muscone and other fragrance precursors were directly prepared with this procedure, while a synthetic route was developed to easily transform a cyclopentenone derivative into trans-Magnolione and dehydro-Magnolione_. The rearrangement of exocyclic allylic alcs. was tested as well, and a dynamic kinetic resolution was observed: α,β-unsaturated ketones with (E)-configuration and a high diastereomeric excess were synthesized. Finally, the 2,2,6,6-tetramethyl-1-piperidinium tetrafluoroborate (TEMPO⁺BF₄^–)/laccase catalyzed oxidative rearrangement was combined with the ene-reductase/alc. dehydrogenase cascade process in a one-pot three-step synthesis of cis or trans 3-methylcyclohexan-1-ol, in both cases with a high optical purity.

Advanced Synthesis & Catalysis 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, Category: piperidines.

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

Loman, Jacob. J. published the artcileA combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic & Biomolecular Chemistry (2016), 14(16), 3883-3888, database is CAplus and MEDLINE.

The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using exptl. and computational methods to gain deeper insight into trends in reactivity.

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

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

Merbouh, Nabyl published the artcileOxoammonium Salts. 9. Oxidative Dimerization of Polyfunctional Primary Alcohols to Esters. An Interesting β Oxygen Effect, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Organic Chemistry (2004), 69(15), 5116-5119, database is CAplus and MEDLINE.

The use of the oxidant 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in combination with pyridine for the oxidative, dimeric esterification of primary alcs. is described. The ester is the predominant product of the reaction with alcs. containing a β oxygen. In the absence of a β oxygen, the corresponding aldehyde is found in appreciable amounts, but a concentration effect can be observed In the absence of pyridine, little ester is formed, and no appreciable reaction takes place with β-oxygenated compounds δ Lactones have been prepared from diethylene glycol and 2,2′-thiodiethanol, without sulfur oxidation

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

Miller, Shelli A. published the artcileCatalytic Oxidation of Alcohols Using a 2,2,6,6-Tetramethylpiperidine-N-hydroxyammonium Cation, Category: piperidines, the publication is European Journal of Organic Chemistry (2019), 2019(6), 1413-1417, database is CAplus.

The oxidation of alcs. to aldehydes, ketones, and carboxylic acids is reported using 2,2,6,6-tetramethylpiperidine-4-acetamido-hydroxyammonium tetrafluoroborate as a catalyst in conjunction with sodium hypochlorite pentahydrate as a terminal oxidant. The reaction is generally complete within 30-120 min using an acetonitrile/water mix as the solvent, and no additives are required. Product yields are good to excellent and of particular note is that the methodol. can be used to access aryl α-trifluoromethyl ketones.

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, Category: piperidines.

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