New Syntheses of Picene

Newman, Melvin S.

doi:10.1021/jo01188a005

Cited by 24 publications

(8 citation statements)

References 11 publications

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“…-Ethyl 3-oxobutanoate (2.44 g, 19 mmol) in dimethoxyethane (20 cm 3 ) was added slowly to a suspension of sodium hydride (740 mg, 18.5 mmol) in dimethoxyethane (7 cm 3 ) at 5 ЊC and under a nitrogen atmosphere. 1-Bromo-2-(1-naphthyl)ethane 15 28 (4.0 g, 17 mmol) in dimethoxyethane (30 cm 3 ) was added dropwise, the cooling bath removed and the reaction mixture stirred at 60 ЊC for 16 h. Sodium chloride solution (10%) (100 cm 3 ) was added, and the product extracted with diethyl ether (3 × 30 cm 3 ). The organic layers were washed with water and dried (MgSO 4 ).…”

Section: Synthesismentioning

confidence: 99%

Photochemistry of substituted cyclic enones. Part 11.1 Synthesis and photophysics of 5-arylalkyl-3-phenylcyclopentenones

Kelly¹,

Doyle²,

Guha³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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The photophysical properties of 3-phenyl-5-[2-(1-naphthyl)ethyl]cyclopent-2-enone and 5-[2-(1-naphthyl)methyl]-3-phenylcyclopent-2-enone have been compared with those of their constituent alkylated chromophores 1-ethylnaphthalene, 3-phenyl-5-(2-phenylethyl)cyclopent-2-enone and 3-phenyl-5-benzylcyclopent-2-enone by means of UV absorption spectroscopy, steady state and time resolved low temperature emission spectroscopy and laser flash photolysis. In mixed solvent low temperature glasses such as ethanol-isopentane-diethyl ether (2 : 5 : 5, v/v) (EPA) phosphorescence decay of all the enones shows multiexponential behaviour consistent with different lifetimes at different solvent sites. The naphthalene derivatives also show a longer lived emission consistent with slow processes involving a naphthalene localised triplet excited state. By contrast in fluid solution flash photolysis experiments reveal that there is rapid equilibration between the enone-and naphthalene-localised states.

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Section: Synthesismentioning

confidence: 99%

Photochemistry of substituted cyclic enones. Part 11.1 Synthesis and photophysics of 5-arylalkyl-3-phenylcyclopentenones

Kelly¹,

Doyle²,

Guha³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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“…Unsere Synthesen der Dehydroverbindungen VIIIa und VIIIc stutzen sich auf Modellversuche mit Naphthyl-2-essigsaure (IV), deren Saurechlorid IVa [9] rnit Natrium-malonsaurediathylester zum Athoxycarbonylacetessigester V fiihrte2), welcher sich mit Polyphosphorsaure zum 2,4-Dihydroxyphenanthren-3-carbonsaureester (VII) cyclisieren liess 3). Alkalische Verseifung und saure Decarboxylierung dieses Esters3) gaben das bekannte 2,4-Dihydroxyphenanthren (VIII) [12].…”

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Welkstoffe und Antibiotika. 40. Mitteilung [1]. Synthesen von Dehydroorchinol‐methyläther und Dehydroorchinol

Müller

Seres

Steiner

et al. 1974

Helvetica Chimica Acta

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Mitteilung [l]Zusanznzenfussung. Die analytisch ermittelte Struktur des Orchinols als 2,4-Dimethoxy-7-hydroxy-9,lO-dihydrophenanthren wurde durch Synthese dcs Dehydroorchinol-methylathers (2,4,7-Trimethoxyphenanthren) VIII a und des Dehydroorchinols (2,4-Dimethoxy-7-hydroxyphenanthren) VIII c eindeutig bestatigt. Unsere Synthesen der Dehydroverbindungen VIIIa und VIIIc stutzen sich auf Modellversuche mit Naphthyl-2-essigsaure (IV), deren Saurechlorid IVa [9] rnit Natrium-malonsaurediathylester zum Athoxycarbonylacetessigester V fiihrte2), welcher sich mit Polyphosphorsaure zum 2,4-Dihydroxyphenanthren-3-carbonsaureester (VII) cyclisieren liess 3). Alkalische Verseifung und saure Decarboxylierung dieses Esters3) gaben das bekannte 2,4-Dihydroxyphenanthren (VIII) [12].Es war offensichtlich, und es wurde durch die Versuche bestatigt, dass die analoge Resktionsfolge rnit 6-Methoxynaphthyl-2-essigsaure ( IVd) zum 2,4-Dihydroxy-7- 1) 2)3)

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“…The Kindler modification (10) of the Willgerodt reaction yielded a solid thiomorpholide which was at once hydrolyzed by a mixture of acetic acid, sulfuric acid, and water (42% over-all yield).…”

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confidence: 99%

1, 10-DIPHENYL-2,9-DIMETHYL-3,4,7,8-TETRAHYDROFURO[3,2-g, 4,5-g']DIISOQUINOLINIUM DIIODIDE

Whaley¹,

White²

1953

J. Org. Chem.

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Japanese interest in the alkaloid cepharanthine as an antitubercular agent led to the synthesis and evaluation of numerous analogs (1). Most of the synthetic work was done by Tomita and the most active compound which he prepared was 2.7bis(piperidylacetyl)dibenzo-p-dioxin (I). A less active compound was 2,8bis(piperidylaeetyl)dibenzofuran (II) (2).Since cepharanthine has its two nitrogen atoms in tetrahydroisoquinoline rings, it was decided to prepare a dibenzofuran derivative having two tetrahydroisoquinoline rings. A compound similar to the type desired was achieved

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New Syntheses of Picene

Abstract: The synthesis of picene, 5-methylpicene, 13-methylpicene, and 13-picenol and the necessary intermediates is described.Columbus, Ohio.

Cited by 24 publications

References 11 publications

Photochemistry of substituted cyclic enones. Part 11.1 Synthesis and photophysics of 5-arylalkyl-3-phenylcyclopentenones

Photochemistry of substituted cyclic enones. Part 11.1 Synthesis and photophysics of 5-arylalkyl-3-phenylcyclopentenones

Welkstoffe und Antibiotika. 40. Mitteilung [1]. Synthesen von Dehydroorchinol‐methyläther und Dehydroorchinol

1, 10-DIPHENYL-2,9-DIMETHYL-3,4,7,8-TETRAHYDROFURO[3,2-g, 4,5-g']DIISOQUINOLINIUM DIIODIDE

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