Phase-Transfer Catalyzed Oxidative Decyanation of α-Secondary Nitriles; A Convenient Synthesis of Aromatic Ketones

Donetti, A.; O, Boniardi; Ezhaya, Antoine

doi:10.1055/s-1980-29301

Cited by 43 publications

(13 citation statements)

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“…Oxidation of 2-arylalkanenitrles (including 1a) with oxygen under PTC conditions to the corresponding phenones is firmly established [27][28][29]. Reactions of 1a carried out either in the presence of more diluted sodium hydroxide solutions or in different solvents and temperatures gave usually lower content of 2a in the reaction mixtures ( Table 2, entries 2-6).…”

Section: Resultsmentioning

confidence: 94%

Difluoromethylation of some C–H acids with chlorodifluoromethane under conditions of phase transfer catalysis (PTC)

Nawrot¹,

Jończyk²

2009

Journal of Fluorine Chemistry

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Section: Resultsmentioning

confidence: 94%

Difluoromethylation of some C–H acids with chlorodifluoromethane under conditions of phase transfer catalysis (PTC)

Nawrot¹,

Jończyk²

2009

Journal of Fluorine Chemistry

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“…). This impurity results from oxidative decyanation of secondary nitrile during S N Ar arylation, as proposed in Scheme . Impurity 4A is an oxidative decyanation product, so the oxygen in the solvent may be a factor.…”

Section: Resultsmentioning

confidence: 99%

An Improved and Efficient Process for the Production of Highly Pure Dexmethylphenidate Hydrochloride

Xing

Shen

Sun

et al. 2016

Journal of Heterocyclic Chem

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“…The air oxidation of benzhydrylcyanides to benzophenones was studied by A. Donetti . For diphenylacetonitrile in DMSO, the oxidation appears to almost exclusively follow pathway A, producing mainly cyanate as a by-product (Scheme ).…”

Section: Racemic R 83842mentioning

confidence: 99%

Development Summary towards a Manufacturable Process for R 83842 [(S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole]

Knaep

Vandendriessche

Daemen

et al. 2000

Org. Process Res. Dev.

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A scalable process to produce enantiomeric R 83842, (S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole, is developed and described as a lecture* transcript. Cheap and safe reagents have been used. A typical procedure for oxidative destruction of aqueous cyanide waste, and stability data on N-acetyl hydrazine are provided. Special focus is on cost analysis as an important tool in developing performant synthetic methods. The method consists of preparing a chiral monosubstituted hydrazine which is ring closed to the chiral 1-alkylated 1,2,4-triazole title compound.

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Phase-Transfer Catalyzed Oxidative Decyanation of α-Secondary Nitriles; A Convenient Synthesis of Aromatic Ketones

Cited by 43 publications

References 0 publications

Difluoromethylation of some C–H acids with chlorodifluoromethane under conditions of phase transfer catalysis (PTC)

Difluoromethylation of some C–H acids with chlorodifluoromethane under conditions of phase transfer catalysis (PTC)

An Improved and Efficient Process for the Production of Highly Pure Dexmethylphenidate Hydrochloride

Development Summary towards a Manufacturable Process for R 83842 [(S)-6-[(4-chlorophenyl) (1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole]

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