Experiments on the synthesis of tetracycline. Part 15. Oxidation of phenols and ring A model phenols to o-hydroxy-dienones with benzeneseleninic anhydride

Barton, D. H. R.; Ley, Steven V.; Magnus, Philip; Rosenfeld, Moshe N.

doi:10.1039/p19770000567

Cited by 46 publications

(20 citation statements)

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“…In search of a solution to futher improve the dimerization yield, it appeared that a reagent capable of delivering an oxygen atom after being fixed on the phenolic oxygen would be ideal for ortho-selective oxygenation. The diphenylseleninic anhydride-mediated Barton oxidation 41,42 was an obvious method to try, but a recent report by Pettus and co-workers 43 on the use of IBX for regioselective ortho-oxygenation of phenols brought us to select this λ 5 -iodane reagent.…”

Section: Methodsmentioning

confidence: 99%

Iodane-mediated and electrochemical oxidative transformations of 2-methoxy- and 2-methylphenols

Quideau¹,

Pouységu²,

Deffieux³

et al. 2003

Arkivoc

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A series of 2-methoxy and 2-methylphenols have been submitted to oxygenative oxidation reactions using (1) the λ 3 -iodane DIB, (2) a non-explosive and non-moisture sensitive version of the λ 5 -iodane IBX, named SIBX for Stabilized IBX, and (3) anodic oxidation with the aim of identifying the best reaction conditions for preparing orthoquinonoid cyclohexadienone synthons. Both the use of DIB and anodic oxidation appeared equally valuable for making orthoquinone dimethyl ketals, but the λ 3 -and λ 5-iodane reagents are more appropriate to induce ortho-oxygenation of 2-methylphenols. In particular, SIBX emerged as a useful reagent for mediating ortho-hydroxylation into dimerizing orthoquinols, a tactic that can be applied to the synthesis of natural bis(monoterpenoids) such as aquaticol.

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Section: Methodsmentioning

confidence: 99%

Iodane-mediated and electrochemical oxidative transformations of 2-methoxy- and 2-methylphenols

Quideau¹,

Pouységu²,

Deffieux³

et al. 2003

Arkivoc

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“…3 However, the formation of hydroxydienones, or of coupled products, dominates in some cases (eq 3). 4 When the reaction is performed with BSA in the presence of Hexamethyldisilazane, the corresponding N-phenylselenoimine is generally obtained, again with high ortho selectivity (eq 4). This provides a means for aromatic amination when used in conjunction with reduction of the imine Dehydrogenation of Carbonyl Compounds.…”

Section: University Of Calgary Calgary Alberta Canadamentioning

confidence: 99%

Benzeneseleninic Acid

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2007

Encyclopedia of Reagents for Organic Synthesis

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“…For the generation of ortho-quinols by selec- tive ortho-hydroxylation of 2-substituted arenols such as 47a-c, one should not forget the selenium-based Barton oxidation, in which oxygenation at the ortho position is ensured by intramolecular delivery from the diphenylseleninic anhydride following reaction of the latter with the phenolate anion ( Figure 15) [81,82]. Acid hydrolysis furnished ortho-quinols that spontaneously dimerized to give bicyclo[2.2.2]octenones 48a-c. Pyrolysis of such dimers can be used to regenerate the ortho-quinol parents in situ [180].…”

Section: Metal-based Oxidative Activationmentioning

confidence: 99%

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

Quideau

2002

Modern Arene Chemistry

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The oxidative activation of arenes is a powerful and versatile synthetic tactic that enables dearomatization to give useful synthons. Central to this chemistry are hydroxylated arenes or arenols, the phenolic functions of which can be exploited to facilitate the dearomatizing process by two-electron oxidation. Suitably substituted arenols can hence be converted, with the help of oxygen-or carbon-based nucleophiles, into ortho-quinone monoketals and ortho-quinols. These 6-oxocyclohexa-2,4-dienones are ideally functionalized for the construction of many complex and polyoxygenated natural product architectures. Today, the inherent and multiple reactivity of arenol-derived ortho-quinone monoketals and orthoquinols species is finding numerous and, in many cases, biomimetic applications in modern organic synthesis. 15.1

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Experiments on the synthesis of tetracycline. Part 15. Oxidation of phenols and ring A model phenols to o-hydroxy-dienones with benzeneseleninic anhydride

Cited by 46 publications

References 0 publications

Iodane-mediated and electrochemical oxidative transformations of 2-methoxy- and 2-methylphenols

Iodane-mediated and electrochemical oxidative transformations of 2-methoxy- and 2-methylphenols

Benzeneseleninic Acid

Oxidative Conversion of Arenols into ortho ‐Quinols and ortho ‐Quinone Monoketals – A Useful Tactic in Organic Synthesis

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