Stoichiometry of the oxidation of primary alcohols with pyridinium chlorochromate. Evidence for a two-electron change

Brown, Herbert C.; Rao, C. Gundu; Kulkarni, Surendra U.

doi:10.1021/jo01329a051

Cited by 47 publications

(17 citation statements)

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“…This is according to the earlier observations with MCC [7,8] and with structurally similar other halochromates [9]. It has already been shown that both pyridinium fluorochromate (PFC) [14] and pyridinium chlorochromate (PCC) [15] act as two-electron oxidants and are reduced to chromium(IV) species by determining the oxidation state of chromium by magnetic susceptibility, electron spin resonance (ESR), and IR studies.…”

Section: Resultssupporting

confidence: 85%

Kinetics and mechanism of the oxidation of some organic sulfides by morpholinium chlorochromate

Malani

Baghmar

Sharma

2008

Int J of Chemical Kinetics

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The oxidation of organic sulfides by morpholinium chlorochromate (MCC) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both MCC and the sulfide. The reaction is catalyzed by toluene-p-sulfonic acid (TsOH). The oxidation was studied in 19 different organic solvents. An analysis of the solvent effect by Swain's equation showed that both the cation-and anion-solvating powers of the solvents play important roles. The correlation analyses of the rate of oxidation of 34 sulfides were performed in terms of various single and multiparametric equations. For the aryl methyl sulfides, the best correlation is obtained with Charton's localized-delocalized-resonance and localized-delocalized-resonancesteric equations. The oxidation of alkyl phenyl sulfides exhibited a very good correlation in terms of the Pavelich-Taft equation. The polar reaction constants are negative, indicating an electrondeficient sulfur center in the rate-determining step. A mechanism involving formation of a sulfonium cation intermediate in the slow step has been proposed.

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Section: Resultssupporting

confidence: 85%

Kinetics and mechanism of the oxidation of some organic sulfides by morpholinium chlorochromate

Malani

Baghmar

Sharma

2008

Int J of Chemical Kinetics

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“…This is according to the earlier observations with structurally similar other halochromates. It has already been shown that both pyridinium fluorochromate (PFC) [15] and pyridinium chlorochromate (PCC) [16] act as twoelectron oxidants and are reduced to chromium(IV) species by determining the oxidation state of chromium by magnetic susceptibility, ESR, and IR studies.…”

Section: Stoichiometrymentioning

confidence: 99%

Oxidation of some α‐hydroxy acids by tetraethylammonium chlorochromate: A kinetic and mechanistic study

Swami

Yajurvedi

Mishra

et al. 2009

Int J of Chemical Kinetics

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The oxidation of glycolic, lactic, malic, and a few substituted mandelic acids by tetraethylammonium chlorochromate (TEACC) in dimethylsulfoxide leads to the formation of corresponding oxoacids. The reaction is first order each in TEACC and hydroxy acids. Reaction is failed to induce the polymerization of acrylonitrile. The oxidation of α-deuteriomandelic acid shows the presence of a primary kinetic isotope effect (k H /k D = 5.63 at 298 K). The reaction does not exhibit the solvent isotope effect. The reaction is catalyzed by the hydrogen ions. The hydrogen ion dependence has the following form:Oxidation of p-methylmandelic acid has been studied in 19 different organic solvents. The solvent effect has been analyzed by using Kamlet's and Swain's multiparametric equations. A mechanism involving a hydride ion transfer via a chromate ester is proposed. C 2009 Wiley Periodicals, Inc. Int J Chem Kinet 42: 50-55, 2010

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“…It was found that the oxidation of compound 9 with manganese dioxide 11 in dichloromethane was not completed even under reflux condition. Therefore, we tried pyridinium chlorochromate as an oxidising agent in dichloromethane at 25-30 °C and obtained the compound 10 25,26 in 87% yield without further purification. The picene-13-carbaldehyde 10 was condensed with active methylene compounds using piperidine as a base to give the title compounds 11-17.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, anti-inflammatory activity of picen-13-ylmethylene derivatives

Shanmuganathan¹,

Prince²,

Dhatchanamoorthy³

et al. 2017

Arkivoc

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Stoichiometry of the oxidation of primary alcohols with pyridinium chlorochromate. Evidence for a two-electron change

Cited by 47 publications

References 0 publications

Kinetics and mechanism of the oxidation of some organic sulfides by morpholinium chlorochromate

Kinetics and mechanism of the oxidation of some organic sulfides by morpholinium chlorochromate

Oxidation of some α‐hydroxy acids by tetraethylammonium chlorochromate: A kinetic and mechanistic study

Synthesis, anti-inflammatory activity of picen-13-ylmethylene derivatives

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