Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO<sub>2</sub>

Bergman, Jan; Engman, Lars

doi:10.1515/znb-1980-0717

Cited by 10 publications

References 9 publications

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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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Organoselenium and Organotellurium Oxidation and Reduction

Młochowski

Lisiak

Wójtowicz‐Młochowska

2011

Patai's Chemistry of Functional Groups

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The Reactivity of Selenium Dioxide Towards Aromatic Aldehydes Hydrazones, Azines and Phenylhydrazones: Carbonyl Regeneration and a New One‐Pot Oxidation of Aldehydes to Aromatic Acids

Dekova

Evers

Christiaens

et al. 1987

Bulletin des Soc Chimique

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Bull. Soc. Chim. Belg. w l . % / n * 311987 0037-96461871 $ 2.00 + 0.00 0 1987 Cellit€ van Beheer van hat Bulletin V . Z . Y . 8. V. h v a l a , H. J. Everala. L . R. Christieensla, and H. R. hill-1b Institute o f Orgmic h i s t r y , 8.6. m d Cyclotron Reaearch Center, 8.30, lhiwraity o f Libgs. Sort-Tilmn. 4OOO Libgs 1, B e l q i u Received : 25/11/1986 -Accepted : 10/12/l986 ABSIRACI Selenium dioxide is a mild oxidizing reagent able, in hot D.H.F. solution, to regenerate arylaldehydes from their hydrazones and azines. The same experimental conditions in the case o f phenylhydrazones of aromatic aldehydes yield the corresponding substituted benzoic acids. In this respect the behaviour of Se02 differs from that of benzeneseleninic anhydride. Oxidation of phenylhydrazines with various reagents has been reported in the literature (2) and the action of selenium dioxide on hydrazine and arylhydrazines has been described by different authors ( 3 ) . Only a small amount of information has appeared concerning the reaction between Se02 and hydrazones and arylhydrazones of aldehydes or ketones. However, selenium dioxide is a cheap, stable and easy to handle reagent. In 1970, F. VENIEN and al. (4) atudied the reactivity o f Se02 in protic solvents (C H OH, CH3-COOH, CH,0(CH2)20H ... ) on nitro and dinitrophenylhydrazone of cyclic or acyclic ketones. They observed that, when the 0 carbon atom to the C=N bond does not bear an hydrogen atom, an a-carbonylated phenylhydrazone is normally formed; in the other cases, a,0-unsaturated hydra-zone8 are obtained. Yields of both reactions are generally low. Sane years ago, D. BARTON ( 5 ) in the course of his work on the regeneration of ketones from arylhydrazones, found that SeO2 in T.H.F. solution was not an "effective alternative reagent to benzene seleninic anhydride (B.5.A.)" which leads to the regeneration of the corresponding ketone with good yields.We wish to report here our results concerning the reactifity of SeO and phenylhydrazones of aromatic aldehydes.

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A Convenient One‐Pot Preparation of Bis(nitroaryl) Tellurides Using a Tellurium‐Copper Couple as the Telluration Reagent

Suzuki

Nakamura

1994

Chem. Ber.

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Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂

Cited by 10 publications

References 9 publications

Organoselenium and Organotellurium Oxidation and Reduction

Organoselenium and Organotellurium Oxidation and Reduction

The Reactivity of Selenium Dioxide Towards Aromatic Aldehydes Hydrazones, Azines and Phenylhydrazones: Carbonyl Regeneration and a New One‐Pot Oxidation of Aldehydes to Aromatic Acids

A Convenient One‐Pot Preparation of Bis(nitroaryl) Tellurides Using a Tellurium‐Copper Couple as the Telluration Reagent

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Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO2

Cited by 10 publications

References 9 publications

Organoselenium and Organotellurium Oxidation and Reduction

Organoselenium and Organotellurium Oxidation and Reduction

The Reactivity of Selenium Dioxide Towards Aromatic Aldehydes Hydrazones, Azines and Phenylhydrazones: Carbonyl Regeneration and a New One‐Pot Oxidation of Aldehydes to Aromatic Acids

A Convenient One‐Pot Preparation of Bis(nitroaryl) Tellurides Using a Tellurium‐Copper Couple as the Telluration Reagent

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Tellurium in Organic Synthesis, IX [15]. Oxidation of Some Nitrogenous Compounds with TeO₂