Dibenzofuran. VIII. Heteronuclear Substitution

Gilman, Henry; Ess, Marian W. Van; Hayes, Dan M.

doi:10.1021/ja01872a030

Cited by 12 publications

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“…The combined early fractions, 15 mg, composed of (GLC) 71% lg, 3% If, and 26% of the reduced diphenyl ether, was chromatographed on silica gel, eluted with hexane, and the eluent (8 mg) was twice recrystallized from chloroform to give 4 mg of lg, 95% pure by GLC, containing 3% If and 2% of the diphenyl ether. The structure of lg is supported by the NMR spectrum (CDC13): 8.5 (s, 1, Hi), 7.85 (s, 1, H4), 7.25-7.8 (m, 3, H6, H7, Hg); mass spectrum m/e 274 (34), 272 (93), 270 (100), 209 (18), 207 (25), 137 (22), 136 (21), 135 (20), 86 (14).…”

Section: Methodsmentioning

confidence: 92%

“…The solid residue was extracted with chloroform and the chloroform solution was washed with 10% sodium hydroxide solution and water, dried, and evaporated to dryness. Two recrystallizations of the residual solid from chloroform afforded 283 mg (29%) of lh as colorless needles: mp 198-200 °C; 99% pure (GLC); NMR (CDC1S) 7.74 (d, 2, J = 3 Hz, , + He), 7.52 (d, 2, J = 3 Hz, H8 + H7); ir (CHC13) 1600,1490,1439,1379,1176,870 cm-1; uv (CHClg) 257 nm (t 17 000), 294 (18 600), 310 (5800), 323 (5800); mass spectrum m/e 308 (55), 306 (100), 304 (86), 243 (21), 241 (22), 171 (22), 153 (22), 152 (18), 121.5 (15), 120.5 (14).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of specific polychlorinated dibenzofurans

Gray¹,

Dipinto²,

Solomon³

1976

J. Org. Chem.

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Comments on Standardization of Chemical Shift Values. In our previous report on the 1H NMR spectra of several of these bicyclic adducts,2 i.e., 18a and 18c, in addition to incorrect assignment of the protons H1-H4, we had some difficulty due to nonlinearity of the field on the C-60 HL. This problem was corrected and standards of known chemical shift were used to calibrate all spectra reported here.

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Section: Methodsmentioning

confidence: 92%

Section: Methodsmentioning

confidence: 99%

Synthesis of specific polychlorinated dibenzofurans

Gray¹,

Dipinto²,

Solomon³

1976

J. Org. Chem.

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“…D u r c h f i i h r u n g d e r S y n t h e s e n Mit dem 2-Joddibenzofuran (V) als Ausgangsprodukt erbrachte die homokondensierende ULLMANN-Reaktion gemaB ( 6 ) das 13,[22][23][24][25][26][27][28][29][30][31][32][33] Unter ganz ahnlichen Bedingungen konnte auch die Synthese der drei Methoxy-oxydo-p-terphenyle XVI, XVII und XVIII vollzogen werden; XVI und XVII aus 2-Joddibenzofuran (V) und o-bzw. p-Jodanisol, X V I I I dagegen aus 2-Jod-3-methoxydibenzofuran (XI) mit Jodbenzol.…”

Section: Die Konstitution Von I Wurde Durch Cberfiihrung In Die Bereiunclassified

“…Die Ausbeute an 2,7-Diaminodibenzofuran (VII) schwankt um 20% d.Th., bezogen auf VI. b) 2,7-Dijoddiheiizofuran (VIII)27,I g 2,7-Diaminodibenzofuran-dihydrochlorid werden in 40 ml konzSalzsaure und 300 ml Wasser in der Kalte mit einer Losung von 14,5 g Natriumnitrit tetrazotiert. Die evtl.…”

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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“…COMPOUND 27. A mixture of 25 grams of 2,5-dimethoxy potassium phenoxide, 0.13M (11), 25 grams of p-fluoronitrobenzene, 0.175M (17), 0.5 grams of 2,5-dimethoxyphenol (11), and 0.2 grams of copper powder was heated in a metal bath at 155-160°f or one hour. The melt was poured into alkaline ice water.…”

mentioning

confidence: 99%

Synthesis of 1,2,3,4-Tetra-O-Acetyl -6- O- Benzhydryl -β- Glucose.

Stanonis¹,

King²

1964

J. Chem. Eng. Data

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in vacuo or quenched in ice water. Residual or precipitated product was dried and recrystallized.Method 8. Amides. METHOD A. COMPOUNDS 35, 37, 39 AND 41. A mixture of 0.1M of dicarbethoxyhomogentisyl chloride and 0.1M of the nitroaniline was refluxed one hour in o-dichlorobenzene. The product usually separated on cooling. Those that did not separate were precipitated by pouring the reaction mixture into hexane. The product was filtered off and recrystallized.

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Dibenzofuran. VIII. Heteronuclear Substitution

Cited by 12 publications

References 0 publications

Synthesis of specific polychlorinated dibenzofurans

Synthesis of specific polychlorinated dibenzofurans

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

Synthesis of 1,2,3,4-Tetra-O-Acetyl -6- O- Benzhydryl -β- Glucose.

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