Chlorous acid oxidation of trifluoromethylphenols: cyclopentenolones by benzilic acid ring contraction

Blazejewski, Jean‐Claude; Dorme, Régine; Wakselman, Claude

doi:10.1039/p19870001861

Cited by 20 publications

(2 citation statements)

References 5 publications

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“…[109][110][111] Concerning the quinone system, there are few literature references reported on the use of trifluoromethyl-substituted benzoquinones as redox systems 112 and as synthons for organic synthesis. 113 The interest in these trifluoromethylated compounds increased and a synthetic route was built up. The alkylation of 2-bromo-3-bromomethyl-1,4dimethoxynaphthalene (154) was carried out with sodium alkoxides in tetrahydrofuran to afford compounds 155 in 90-95% yield (Scheme 29).…”

Section: Synthesis Of 2-alkoxymethyl-3-trifluoromethyl-14-naphthoquinonesmentioning

confidence: 99%

A Survey of Synthetic Routes towards the Pyranonaphthoquinone Antibiotic Pentalongin and Syntheses of the Corresponding Nitrogen Derivatives

Claessens¹,

Verniest²,

Jacobs³

et al. 2007

Synlett

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A survey through the synthetic possibilities of pentalongin and its derivatives is presented. Pentalongin is the parent compound in the 3,4-dehydropyranonaphthoquinone series and is the active principle of the medicinal plant Pentas longiflora. Attention is paid to eight approaches towards these 3,4-dehydropyranonaphthoquinones. Synthetic methodologies for the corresponding nitrogen analogues are described, focusing on several natural products.

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Section: Synthesis Of 2-alkoxymethyl-3-trifluoromethyl-14-naphthoquinonesmentioning

confidence: 99%

A Survey of Synthetic Routes towards the Pyranonaphthoquinone Antibiotic Pentalongin and Syntheses of the Corresponding Nitrogen Derivatives

Claessens¹,

Verniest²,

Jacobs³

et al. 2007

Synlett

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“…The Et 3 SiH/TFA system reduces the polyfunctional cyclic α,β-enone in Eq. 276 without affecting the α-hydroxy carboxyl or α-chloro keto groups 453. The use of PMHS/TFA and a base leads to the 1,4-reduction of enones (Eq.…”

mentioning

confidence: 99%

Ionic and Organometallic‐Catalyzed Organosilane Reductions

2009

Ionic and Organometallic‐Catalyzed Organosilane Reductions

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Ionic and Organometallic‐Catalyzed Organosilane Reductions

Larson

Fry²

2008

Organic Reactions

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This chapter presents a critical review of synthetically useful variations of ionic methods for hydrogenation of organic compounds. In practice ionic hydrogenation involves the formal introduction of hydride from a donor source to an electron‐deficient carbon center. In this chapter, organosilicon hydrides are used as the source of ionic hydride with the goal of completing and updating earlier review work. Organosilicon compounds with at least one Si‐H bond have the ability to serve as mild‐air and water‐stable sources of hydrides and, thus, have reducing properties. In general, organosilicon hydrides do not undergo spontaneous reactions with organic compounds unless the organic substrate is a reasonably strong electrophile or the silane is first activated by the interaction of a nucleophilic species with a nucleophilic center. The organosilicon hydrides are covalent compounds that have little or no nucleophilic properties on their own. The use of these hydrides often provides a means of effecting reductions of organic substrates under very mild conditions and with excellent functional group selectivity. Consideration of the nature of the Si‐H bonds provides insight into the chemical behavior of these hydrides. Enhanced hydridic nature manifests itself in the chemical behavior of hydrosilanes.

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Chlorous acid oxidation of trifluoromethylphenols: cyclopentenolones by benzilic acid ring contraction

Cited by 20 publications

References 5 publications

A Survey of Synthetic Routes towards the Pyranonaphthoquinone Antibiotic Pentalongin and Syntheses of the Corresponding Nitrogen Derivatives

A Survey of Synthetic Routes towards the Pyranonaphthoquinone Antibiotic Pentalongin and Syntheses of the Corresponding Nitrogen Derivatives

Ionic and Organometallic‐Catalyzed Organosilane Reductions

Ionic and Organometallic‐Catalyzed Organosilane Reductions

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