Dibenzofuran. III. Nuclear Substitutions

Gilman, Henry; Brown, Gordon E.; Bywater, W. G.; Kirkpatrick, W. H.

doi:10.1021/ja01326a081

Cited by 25 publications

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“…A 38% yield of 2,8-dichlorodibenzofuran melting at 185°has been reported for the chlorination of dibenzofuran with chlorine in carbon tetrachloride without catalyst (1).…”

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confidence: 97%

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The Chlorination of Dibenzofuran and Some of Its Derivatives

Oita¹,

Johnson²,

Gilman³

1955

J. Org. Chem.

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“…A 38% yield of 2,8-dichlorodibenzofuran melting at 185°has been reported for the chlorination of dibenzofuran with chlorine in carbon tetrachloride without catalyst (1).…”

mentioning

confidence: 97%

“…1 ,S-Dichloro-4-hydroxydibenzofuran. The chlorination was carried out according to the h i b i t e d .…”

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confidence: 99%

The Chlorination of Dibenzofuran and Some of Its Derivatives

Oita¹,

Johnson²,

Gilman³

1955

J. Org. Chem.

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“…The preparation of 2,8-dichlorodibenzofuran was carried out as described (2). Three crystallizations were necessary to remove tri-and tetrachlorodibenzofuran from the product.…”

Section: Methodsmentioning

confidence: 99%

Acute and Chronic Oral Toxicity of Chlorinated Dibenzofurans to Salmonid Fishes

Zitko¹,

Wildish²,

Hutzinger³

et al. 1973

Environmental Health Perspectives

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A median mortality of 120 ± 30 days occurred among juvenile Atlantic salmon (Salmo salar), fed dry fish food containing 2.7, 5.7, 2.8, and 9.1 uMg/g wet weight of 2,8-di-, tri-, tetra-, and octachlorodibenzofuran, respectively (1). Only octachlorodibenzofuranx was detected in the dead fish, and the level was 0.03 ug/g in the muscle and 0.21 ,Ag/g in the gut (both values on wet weight basis). The fate of the lower chlorinated dibenzofurans was not known and additional experiments, described in this paper, were carried out with immature brook trout (Salvelinus fontinalis), fed relatively high levels of 2,8-dichlorodibenzofuran. ExperimentalThe preparation of 2,8-dichlorodibenzofuran was carried out as described (2). Three crystallizations were necessary to remove tri-and tetrachlorodibenzofuran from the product.

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“…Aber erst SCHIMMELSCHMIDT 15) gelang es, brauchbare experimentelle Bedingungen zu finden *). Auf der Basis dieser Kupplungsreaktion wurde von ihm auch der mit (12) bezeichnete Weg zur Dibenzofuranreihe eroffnet. Besonders bemerkenswert ist der in einer Kalischmelze gemaB (12 b) eintretende OxydoringschluS.…”

Section: Synthesen Nach Schimmelschmidt L5)unclassified

Synthese und eigenschaften von oxydo‐p‐oligophenylenen. 18. Mitteilung über poly‐ und oligophenylene

1965

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ZUSAMMENFASSUNG:Oxydosubstituierte p-Oligophenylene leiten sich vom Dibenzofuran ab, sind also briikkensubstituierte Oligophenylene. Ihre Darstellung erfolgte mit Hilfe der ULLMANN-Re&-tion unter Verwendung von Jodderivaten des Dibenzofurans; zu deren Darstellung dienten entsprechende Aminoverbindungen.Einige Oxydo-p-oligophenylene wurden auf der Grundlage der Kupplungs-Reaktion von o-Chlorphenyl-diazoniumverbindungen mit p-Benaochinon und nachfolgendem Oxydoringschlul3 an daraus hervorgehenden 2-Chlor-2'-hydroxybiarylen erhalten. Als weitere RingschluB-Reaktion wurde die dehydratisierende Atherspaltung von 2,2'-Dimethoxybiarylen angewandt. Damit konnte die Synthese eines Trioxydo-p-quaterphenyls, eines durchgehend uberbruckten Quaterphenylderivates, verwirklicht werden. Die Darstellung des entsprechenden Dioxydo-p-terphenyles gelang nach der EBELschen Dibenzofuransynthese.Die vollstandige oberbriickung fiihrt ZZI verminderter Loslichkeit und erhohtem Schmelzpunkt. Durch die gleichzeitige Substitution mit Methoxylgruppen war es in mehreren Fallen moglich, die Loslichkeit zu verbessern.Die Bruckensubstitution fiihrt zu langwelligen Elektronenbanden. Bei vollstandiger cberbruckung werden UV-Absorptionsbanden (Konjugationsbanden) beobachtet, die betrachtlich langerwellig sind als die der unsubstituierten Grundkorper. Von der Rotverschiebung der UV-Absorptionsbanden sind auch die Emissionsbanden betroffen: daher zeigen fast alle Oxydo-p-oligophenylene eine intensive blaue Lumineszenz. SUMMARY:Oxido-substituted p-oligophenylenes are derivatives of dibenzo€uran; thus, they are bridge-substituted oligophenylenes. Synthesis was carried out by means of the ULLMANN reaction using iodine derivatives of dibenzofuran which in turn were prepared from the corresponding amino compounds. diazonium compounds with p-benzoquinone and subsequent oxido-ring closure of the resulting 2-chloro-2'-hydroxy-biaryls. Dehydrating ether cleavage of 2,2'-dimethoxy-biaryls was applied as a further method of ring closure. Thus, synthesis of a trioxido-p-quaterphenyl a per-bridged quaterphenyl derivative was accomplished. Preparation o€ the corresponding dioxido-p-terphenyl succeeded with satisfactory yield by means of EBEL'S dibenzofuran synthesis.

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Dibenzofuran. III. Nuclear Substitutions

Cited by 25 publications

References 0 publications

The Chlorination of Dibenzofuran and Some of Its Derivatives

The Chlorination of Dibenzofuran and Some of Its Derivatives

Acute and Chronic Oral Toxicity of Chlorinated Dibenzofurans to Salmonid Fishes

Synthese und eigenschaften von oxydo‐p‐oligophenylenen. 18. Mitteilung über poly‐ und oligophenylene

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