The oxidative rearrangement of 5α-cholestan-3-one

Hellman, Henry M.; Jerussi, Robert A.

doi:10.1016/s0040-4020(01)98633-8

Cited by 11 publications

(1 citation statement)

References 13 publications

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“…Ring transformations using H 2 O 2 /SeO 2 resulted in the ring contraction of cycloalkanones to norcycloalkane carboxylic acids [193,194], and related rearrangements in acyclic ketones [193][194][195][196][197] as well as 3-ketosteroids [198,199]. Moreover, it was observed that ketal 53 was rapidly converted, in high yield, into the -enollactone 54.…”

Section: Selenium(iv) and Tellurium(iv) Oxidementioning

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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Section: Selenium(iv) and Tellurium(iv) Oxidementioning

confidence: 99%

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

Młochowski¹

2011

TOCATJ

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TheBaeyer–VilligerOxidation of Ketones and Aldehydes

1993

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The oxidative conversion of alicyclic ketones into lactones with permonosulfuric acid was discovered by Baeyer and Villiger in 1899, and in their honor the general process by which ketones are converted into esters or lactones is now known as the Baeyer–Villiger reaction. The literature on this synthetically useful process has been reviewed comprehensively through 1953 in Volume 9 of Organic Reactions , and less comprehensive reviews of the reaction have appeared since then. More recent investigations have led to the development of new synthetic reagents, to improvements in experimental reaction conditions, and to a better understanding of regiochemical and stereochemical aspects of the reaction. Baeyer–Villiger reactions now often can be carried out with functional group chemoselectivity and regiochemical control. Although the recent removal from commerce of 90% hydrogen peroxide and reagents based upon this oxidant are a setback to Baeyer–Villiger reaction methodology, alternative reagents, catalysts, and methods described in this review are available to fill the gaps. The definition of the Baeyer–Villiger reaction is somewhat fuzzy, and can be considered to include both ketones and aldehydes. In addition to the traditional use of organic and inorganic peracids as oxidants, examples of oxygen insertion reactions using hydrogen peroxide, alkyl peroxides, and several metal ion oxidants are considered to fall within the scope of this chapter and are included in the tabular survey.

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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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The oxidative rearrangement of 5α-cholestan-3-one

Cited by 11 publications

References 13 publications

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

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

TheBaeyer–VilligerOxidation of Ketones and Aldehydes

Organoselenium and Organotellurium Oxidation and Reduction

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