Catalytic Oxidative Domino Degradation of Alkyl Phenols Towards 2- and 3-Substituted Muconolactones

Giurg, Mirosław; Kowal, Ewa; Muchalski, Hubert; Syper, Ludwik; Młochowski, J.

doi:10.1080/00397910802369687

Cited by 10 publications

(6 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similar ring-degradation took place, when substituted naphthalenes were oxidized. Cinnamic acid or benzofurane derivatives were the final products [160,161].…”

Section: Organoselenium Compounds As Oxidizing Agents and Oxidatiomentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

Self Cite

View full text Add to dashboard Cite

A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as "green reagents" for the oxidation of different organic functional groups. The topic of oxidations catalyzed by organoselenium derivatives has rapidly expanded in the last fifteen years This paper is devoted to the synthetic applications of the oxidation reactions mediated by selenium compounds such as selenium(IV) oxide, areneseleninic acids, their anhydrides, selenides, diselenides, benzisoselenazol-3(2H)-ones and other less often used other organoselenium compounds. All these compounds have been successfully applied for various oxidations useful in practical organic syntheses such as epoxidation, 1,2-dihydroxylation, and α-oxyfunctionalization of alkenes, as well as for ring contraction of cycloalkanones, conversion of halomethyl, hydroxymethyl or active methylene groups into formyl groups, oxidation of carbonyl compounds into carboxylic acids and/or lactones, sulfides into sulfoxides, and secondary amines into nitrones and regeneration of parent carbonyl compounds from their azomethine derivatives. Other reactions such as dehydrogenation and aromatization, active carbon-carbon bond cleavage, oxidative amidation, bromolactonization and oxidation of bromide for subsequent reactions with alkenes are also successfully mediated by selenium (IV) oxide or organoselenium compounds. The oxidation mechanisms of ionic or free radical character depending on the substrate and oxidant are discussed. Coverage of the literature up to early OPEN ACCESSMolecules 2015, 20 10206 2015 is provided. Links have been made to reviews that summarize earlier literature and to the methods of preparation of organoselenium reagents and catalysts.

show abstract

“…Similar ring-degradation took place, when substituted naphthalenes were oxidized. Cinnamic acid or benzofurane derivatives were the final products [160,161].…”

Section: Organoselenium Compounds As Oxidizing Agents and Oxidatiomentioning

confidence: 99%

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…Oxidation of phenols has been extensively studied. − In particular, protocols for the oxidation of phenols to the corresponding ring-opened products, namely, muconic acids, are rather limited . When naphthalenes undergo ring-opening oxidation, ortho -substituted cinnamaldehydes/cinnamic acids are obtained .…”

mentioning

confidence: 99%

Synthesis of o-Carboxyarylacrylic Acids by Room Temperature Oxidative Cleavage of Hydroxynaphthalenes and Higher Aromatics with Oxone

Parida

Moorthy

2015

J. Org. Chem.

View full text Add to dashboard Cite

A simple procedure for the synthesis of a variety of o-carboxyarylacrylic acids has been developed with Oxone (2KHSO5·KHSO4·K2SO4); the oxidation reaction involves the stirring of methoxy/hydroxy-substituted naphthalenes, phenanthrenes, anthracenes, etc. with Oxone in an acetonitrile-water mixture (1:1, v/v) at rt. Mechanistically, the reaction proceeds via initial oxidation of naphthalene to o-quinone, which undergoes cleavage to the corresponding o-carboxyarylacrylic acid. The higher aromatics are found to yield carboxymethyl lactones derived from the initially formed o-carboxyarylacrylic acids.

show abstract

“…Similar ring-degradation took place when substituted naphthalenes were oxidized. Cinnamic acid or benzofurane derivatives were the final products [241,242,247] (Scheme 19).…”

Section: -Nitro-and 24-dinitrobenzeneseleninic Acids 2-no 2 C 6 H 4mentioning

confidence: 99%

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

Młochowski¹

2011

TOCATJ

View full text Add to dashboard Cite

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.

show abstract

Catalytic Oxidative Domino Degradation of Alkyl Phenols Towards 2- and 3-Substituted Muconolactones

Cited by 10 publications

References 20 publications

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

Synthesis of o-Carboxyarylacrylic Acids by Room Temperature Oxidative Cleavage of Hydroxynaphthalenes and Higher Aromatics with Oxone

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

Contact Info

Product

Resources

About