Pyridinium Chlorochromate

Piancatelli, Giovanni; Luzzio, Frederick A.

doi:10.1002/047084289x.rp288.pub2

Cited by 4 publications

(5 citation statements)

References 100 publications

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“…The effect of several alternative solvents on the D:E product ratio was examined, but none performed as well as dichloromethane (cf. entries 9,[13][14][15][16][17]. Nevertheless, moderate to good yields of product can be obtained in both halogenated and nonpolar solvents.…”

Section: Resultsmentioning

confidence: 99%

“…8 N-Alkyl, 9 N-acyl, 10 N-fluoro, 11 N-oxide, 12 and other N-activated pyridinium salts 13 promote a broad range of valuable transformations or act as building blocks for cycloadditions, rearrangements, reductions, oxidations, transition metal couplings, and nucleophilic additions. 14 Protonated pyridinium salts such as pyridinium p-toluenesulfonate (PPTS), 15 a mild organic soluble acid, and pyridinium chlorochromate (PCC), 16 a mild organic soluble oxidant, represent two mainstay reagents in organic synthesis. In addition to synthetic applications, pyridinium salts have been exploited for their physicochemical properties as surfactants, phase transfer agents, optoelectronics, and dyes, and for their biological activities as antimicrobial agents.…”

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confidence: 99%

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Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis

Blades¹,

McConnell²,

Rodrigues³

et al. 2019

Preprint

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<div>N-Quaternized ketene N,O-acetals are typically an unstable, transient class of compounds most commonly observed as reactive intermediates. In this report, we describe a general approach to a variety of benchstable N-quaternized ketene N,O-acetals via treatment of pyridine or aniline bases with ethoxyacetylene and an appropriate Brønsted or Lewis acid (triflic acid, triflimide, or scandium(III) triflate). The resulting pyridinium and anilinium salts may be used as reagents or synthetic intermediates in multiple reaction types. For example, N-(1-ethoxyvinyl) pyridinium or anilinium salts can thermally release highly reactive O-ethyl ketenium ions that undergo electrophilic aromatic substitution with electron rich arenes. N-(1-ethoxyvinyl)-2-halopyridinium salts can also be utilized in peptide couplings as a derivative of Mukaiyama reagents, or react with alcohol and amines in nucleophilic aromatic substitutions.</div>

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis

Blades¹,

McConnell²,

Rodrigues³

et al. 2019

Preprint

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“…1,2 Though the most popular process mediated by PCC is the oxidation of primary and secondary alcohols to aldehyde and ketones, respectively, many other functional groups undergo PCC oxidation. As a continuation of our interest in oxidative processes mediated by transition metal oxo-species [3][4][5][6][7][8][9][10][11] as well as in the synthesis and derivatization of new THF-containing compounds, [12][13][14][15][16][17][18][19][20][21] we recently focused on oxidation processes mediated by PCC.…”

Section: Introductionmentioning

confidence: 99%

Pyridinium chlorochromate chemistry. New insight into oxidation of tetrahydrofurans

Zaccaria¹,

Borbone²,

Oliviero³

et al. 2017

Arkivoc

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A thorough investigation of the minor oxidation products of two penta-tetrahydrofuran compounds with pyridinium chlorochromate has been carried out. Isolation of ring-B oxygenated spiroketal and degradation products, including polycyclic mono-and bis-lactone compounds, supports the previously postulated involvement of cyclic enolether intermediates in the oxidation of THF and poly-THF substances with PCC. Based on the collected evidence, a new mechanistic route for the PCC-mediated oxidative cleavage of -hydroxy-THF compounds to -lactones has been postulated. The proposed mechanism well agrees with the one reported for the oxidative cleavage of 8-hydroxy-neoisocedranol oxide by RuO4, a fact that further supports our previous observation on the similar oxidizing behaviour shown by PPC and RuO4 towards THFcontaining compounds.

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Section: Table 1 -Evaluation Of Reaction Parameters For the Synthesis Of N-(1-ethoxyvinyl) 2-chloropyridinium Salts Dmentioning

confidence: 99%

Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis

McConnell¹,

Blades²,

Rodrigues³

et al. 2021

Preprint

View full text Add to dashboard Cite

N-Quaternized ketene N,O-acetals are typically an unstable, transient class of compounds most commonly observed as reactive intermediates. In this report, we describe a general synthetic approach to a variety of bench-stable N-quaternized ketene N,O-acetals via treatment of pyridine or aniline bases with acetylenic ethers and an appropriate Brønsted or Lewis acid (triflic acid, triflimide, or scandium(III) triflate). The resulting pyridinium and anilinium salts can be used as reagents or synthetic intermediates in multiple reaction types. For example, N-(1-ethoxyvinyl)pyridinium or anilinium salts can thermally release highly reactive O-ethyl ketenium ions for use in acid catalyst-free electrophilic aromatic substitutions. N-(1-Ethoxyvinyl)-2-halopyridinium salts can be employed in peptide couplings as a derivative of Mukaiyama reagents or react with amines in nucleophilic aromatic substitutions under mild conditions. These preliminary reactions illustrate the broad potential of these currently understudied compounds in organic synthesis.

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Pyridinium Chlorochromate

Cited by 4 publications

References 100 publications

Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis

Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis

Pyridinium chlorochromate chemistry. New insight into oxidation of tetrahydrofurans

Synthesis of Bench-Stable N-Quaternized Ketene N,O-Acetals and Preliminary Evaluation as Reagents in Organic Synthesis

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