Azoxybenzene

Bigelow, H. E.; Palmer, Albert W.

doi:10.1002/0471264180.os011.04

Cited by 4 publications

(3 citation statements)

References 9 publications

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“…The use of alkaline glucose to synthesize azoxybenzene from nitrobenzene is an Organic Syntheses procedure [10] and the use of glucose and sucrose to this end has been recorded elsewhere [11,12]. High yield deaminations (replacement of a diazonium group by hydrogen) of aromatic amines via reaction of alkaline glucose [13] and sucrose [14] with diazonium salts have been communicated.…”

Section: Introductionmentioning

confidence: 99%

Reactions of phthalonitriles with carbohydrates and alkali: phthalocyanine and oligomer formation

Tsai

Sandman

2001

J. Porphyrins Phthalocyanines

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Reducing sugars and sodium hydroxide react with phthalonitrile and 4-methoxyphthalonitrile to form mixtures of the phthalocyanine and oligomers. The oligomers, obtained in yields up to 54%, were deduced to have a structure that is predominantly polyazine with the o-cyanophenyl group as a substituent from elemental analysis and spectral data. Since carbohydrate related compounds lacking the reducing linkage gave no products, it is suggested that the observed reactions require the a-hydroxycarbonyl grouping.

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Section: Introductionmentioning

confidence: 99%

Reactions of phthalonitriles with carbohydrates and alkali: phthalocyanine and oligomer formation

Tsai

Sandman

2001

J. Porphyrins Phthalocyanines

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“…The oxidized counterpart of the azo functional group is the azoxy group, wherein one of the two nitrogen atoms is connected to a further oxygen atom with the nitrogen‐nitrogen double bond remaining in place [5,6] . Already in 1931, Bigelow and Palmer reported on a 100 g synthesis of azoxy benzene via reduction of nitro benzene with arsenious oxide in boiling sodium hydroxide solution [7] …”

Section: Introductionmentioning

confidence: 99%

Azoxy Compounds—From Synthesis to Reagents for Azoxy Group Transfer Reactions

Cai,

Empel,

Yao

et al. 2023

Angew Chem Int Ed

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The azoxy functional group is an important structural motif and represents the formally oxidized counterpart of the azo group. Azoxy compounds find numerous applications ranging from pharmaceuticals to functional materials, yet their synthesis remains underdeveloped with a main focus on the formation symmetric azoxy compounds. To overcome challenges in the synthesis of such unsymmetric azoxy compounds, we designed a process employing readily accessible nitroso compounds and iminoiodinanes. This method builds on the use of visible light irradiation to generate a triplet nitrene from iminoiodinanes, which is trapped by nitroso arenes to give access to sulfonyl‐protected azoxy compounds with a good substrate scope and functional group tolerance. We further describe two applications of these sulfonyl‐protected azoxy compounds as radical precursors in synthesis, where the whole azoxy group can be transferred and employed in C(sp3)‐H functionalization of ethers or 1,2‐difunctionalization of vinyl ethers. All of the reactions occurred at room temperature under visible light irradiation without the addition of any photoredox catalysts and additives. Control experiments, mechanism investigations, and DFT studies well explained the observed reactivity.

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“…Aromatic azoxy compounds are key materials for electronic devices based on their liquid crystalline properties, while azo compounds are important as the backbone for a variety of dyestuffs. Azoxyarenes 2 are obtained directly from nitroarenes 1 by heating with alcoholic KOH, sodium alkoxide, or zinc/NaOH, reduction with sodium borohydride, lithium aluminum hydride or sodium arsenite, treatment with magnesium, samarium, or thallium metal in alcohol, catalytic reduction over palladium, alkaline reduction with phosphine or glucose, and electrochemical reduction . Aromatic azo compounds 3 are directly obtainable from nitro compounds 1 by reduction with zinc/NaOH, lithium aluminum hydride 21 or dicobalt octacarbonyl, and by high-temperature reaction with ethanolamines …”

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confidence: 99%