Baeyer-Villiger Reaction of Benzaldehydes Possessing Oxygen Functions with SeO&lt;SUB&gt;2&lt;/SUB&gt;-H&lt;SUB&gt;2&lt;/SUB&gt;O&lt;SUB&gt;2&lt;/SUB&gt;

Nishioka, Hiromi; Katsuno, Keiko; Fujii, Masako; Nishita, Yoshitaka; Koshiba, Natsuko; Harayama, Takashi

doi:10.1248/yakushi1947.119.7_519

Cited by 6 publications

(3 citation statements)

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“…The use of hydrogen peroxide has many advantages: it is safe, cheap, the active oxygen content is high, it does not require a buffer, and it is clean, since the byproduct formed is water. Reports on this particular subject comprise homogeneous catalysts based on Se, As, Mo, Re, Pt, Zr, or (soluble) acid and heterogeneous catalysts containing As, or Se, titanium silicalite, or solid acids . In most cases there are one or more drawbacks, for instance, low activity or selectivity of the catalyst, high cost of the catalyst, or the need for anhydrous hydrogen peroxide.…”

Section: Introductionmentioning

confidence: 99%

“…Among the first catalysts to be used for the epoxidation and Baeyer−Villiger reactions with H 2 O 2 were the substituted benzeneseleninic acids reported by Syper . He investigated the effect of nitro substituents at the ortho and para position of benzeneseleninic acid, obtaining optimum results when only one nitro substituent was present in the ortho position.…”

Section: Introductionmentioning

confidence: 99%

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Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution¹

et al. 2001

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Several diselenides were tested for catalytic activity in Baeyer-Villiger reactions with 60% aqueous hydrogen peroxide. Bis[3,5-bis(trifluoromethyl)phenyl] diselenide forms the corresponding 3,5-bis(trifluoromethyl)benzene seleninic acid in situ, which is a highly reactive and selective catalyst for the oxidation of carbonyl compounds in 1,1,1,3,3,3-hexafluoro-2-propanol, 2,2,2-trifluoroethanol, or dichloromethane.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution¹

et al. 2001

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“…The Baeyer-Villiger reaction using H 2 O 2 /SeO 2 for various benzaldehydes possessing hydroxy or methoxy substituents mainly in ortho and para position, and/or a furan ring, afforded phenols rapidly in good yield or mixtures of the phenols and carboxylic acids. On the other hand, meta-substituted benzaldehydes or benzaldehydes carrying less effective electron donating groups, electrondeficient heteroaromatic and aliphatic aldehydes were oxidized to the corresponding carboxylic acids [200,202,203].…”

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confidence: 99%

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

Młochowski¹

2011

TOCATJ

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Oxidation of different groups of organic compounds, with hydroperoxides catalyzed by non-heavy metal containing low-molecular-weight compounds and enzymes is reviewed. This article is concentrated mainly on the hydrogen peroxide and tert-butyl hydroperoxide, however other less common hydroperoxides are also mentioned. Since hydroperoxides themselves are inactive toward most of the organic substrates, in situ activation of the oxidant is necessary. For this purpose various activators have been applied in stoichiometric or catalytic amounts. The carboxylic acids, nitriles, amides and urea are representative for the first category. The organocatalysts such as-halo carbonyl compounds, ketones, imines, iminium salts, nitroxyl radicals and polyaminoacids, selenium compounds and enzymes are presented. They are involved in oxygen, and electron transfer processes whose mechanisms are briefly discussed, and their applications in laboratory and industrial synthesis are indicated.

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Organoselenium and Organotellurium Oxidation and Reduction

Młochowski

Lisiak

Wójtowicz‐Młochowska

2011

Patai's Chemistry of Functional Groups

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Oxygenated and reduced selenium and tellurium compounds, particularly thoese of practical importance have been extensively investigated especially during the last few decades. Selenium(IV) oxide, selenoxides, selenones, seleninic and peroxyseleninic acids, selenenamides and seleninamides are involved in oxyfunctionalization of unsaturated hydrocarbons, their derivatives, alkylarenes, sulfides and amines, carbon‐oxygen and carbon‐carbon bond cleavage, ring closure and ring transformations, syn ‐elimination, sigmatropic [2,3]‐rearrangement and other, chemo‐ regio‐ and stereocontrolled reactions. The chemistry of oxygenated tellurium compounds has been less extensively explored than their selenium counterparts;, nevertheless some of them have been successfully used for oxyfunctionalization of different groups of organic compounds while telluroxide elimination has gained more attention in the last years becoming a well‐established method for the synthesis of olefins. Hydrogen selenide and telluride, alkali selenides and tellurides, selenoles and telluroles are the most common reduced derivative of these elements. Their properties are expressed in many reactions such as reduction and deoxygenation of different groups of organic compounds alkenes, alkynes, ethers, carbonyl compounds, esters, lactones, oxiranes, nitrogen, sulfur and halogen compounds, as well as dealkylation of tertiary amines. The method for preparation of the different oxygenated and reduced selenium and tellurium compounds are described, their reactions are reviewed, their usefulness in synthesis is indicated and more representative mechanisms are discussed.

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Baeyer-Villiger Reaction of Benzaldehydes Possessing Oxygen Functions with SeO<SUB>2</SUB>-H<SUB>2</SUB>O<SUB>2</SUB>

Cited by 6 publications

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Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution¹

Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution¹

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

Organoselenium and Organotellurium Oxidation and Reduction

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Baeyer-Villiger Reaction of Benzaldehydes Possessing Oxygen Functions with SeO<SUB>2</SUB>-H<SUB>2</SUB>O<SUB>2</SUB>

Cited by 6 publications

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Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution1

Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution1

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

Organoselenium and Organotellurium Oxidation and Reduction

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Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution¹

Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution¹