The Reaction of Ketones with Iodine and Pyridine

Lc, King; McWhirter, Margaret; Rl, Rowland

doi:10.1021/ja01181a071

Cited by 19 publications

(7 citation statements)

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“…[55] 3-Acetylisoqulinoline was prepared from 3-hydroxyisoqulinoline by a Heck reaction. [56] 1-(2-(3'-Isoquinolinyl)-2-oxoethyl)pyridinium iodide was prepared by heating 3-acetylisoqulinoline with excess I 2 in pyridine for 2 h. [57][58][59] 3-Dimethylamino-1-(2'-naphthyl)propanone hydrochloride salt was synthesized by refluxing 2-acetylnaphthalene, paraformaldehyde and dimethylamine hydrochloride in the presence of conc. HCl in 95 % ethanol for 24 h. [59] The a,b-unsaturated ketones were prepared according to literature methods.…”

Section: Methodsmentioning

confidence: 99%

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

Kui

Sham

Cheung

et al. 2006

Chemistry A European J

161

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The crystal structures and photophysical properties of mononuclear [(RC N N)PtX](ClO4)n ((RC N N)=3-(6'-(2''-naphthyl)-2'-pyridyl)isoquinolinyl and derivatives; X=Cl, n=0; X=PPh(3) or PCy(3), n=1), dinuclear [(RC N N)2Pt2(mu-dppm)](ClO4)2 (dppm=bis(diphenyphosphino)methyl) and trinuclear [(RC N N)3Pt3(mu-dpmp)](ClO4)3 (dpmp=bis(diphenylphosphinomethyl)phenylphosphine) complexes are presented. The crystal structures show extensive intra- and/or intermolecular pipi interactions; the two (RC N N) planes of [(RC N N)2Pt2(mu-dppm)](ClO4)2 (R=Ph, 3,5-tBu2Ph or 3,5-(CF3)2Ph) are in a nearly eclipsed configuration with torsion angles close to 0 degrees. [(RC N N)PtCl], [(RC N N)2Pt2(mu-dppm)](ClO4)2, and [(RC N N)3Pt3(mu-dpmp)](ClO4)3 are strongly emissive with quantum yields of up to 0.68 in CH2Cl2 or MeCN solution at room temperature. The [(RC N N)PtCl] complexes have a high thermal stability (T(d)=470-549 degrees C). High-performance light-emitting devices containing [(RC N N)PtCl] (R=H or 3,5-tBu2Ph) as a light-emitting material have been fabricated; they have a maximum luminance of 63,000 cd m(-2) and CIE 1931 coordinates at x=0.36, y=0.54.

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Section: Methodsmentioning

confidence: 99%

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

Kui

Sham

Cheung

et al. 2006

Chemistry A European J

161

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“…It should be noted that the possible intermediate V, obtained from III in the presence of excess iodine and pyridine, can also be transformed into carboxylic ester VI. In order to further confirm the reaction mechanism, we synthesized 1-(4-methoxyphenacyl)pyridinium iodide (6) according to a reported method 13 and investigated the effect of base on the yield of ethyl 4-methoxybenzoate (7) in refluxing ethanol. As shown in Table 2, heating the ethanol solution of 6 without any base at reflux for 24 h, no expected product was detected by thin-layer chromatography (TLC) analysis (Entry 1).…”

Section: Resultsmentioning

confidence: 99%

“…mp 213-215 C (lit. 13 8, 164.2, 146.1, 130.7, 127.8, 126.2, 114.4, 66.0, 55.9 (10 resonances expected, 9 observed); IR (KBr): 1677, 1605, 1247, 1176, 1027 cm À1 .…”

Section: Methodsmentioning

confidence: 96%

“…1-(4-Methoxyphenacyl)pyridinium Iodide (6). 13 A mixture of p-methoxyacetophenone 1 (7.5 g, 0.05 mol), iodine (12.7 g, 0.05 mol), and pyridine (50 mL) was heated at 100 C for 3 h and allowed to stand overnight. The reaction mixture was filtered then thoroughly washed with 40 mL ether to remove unreacted starting substrate.…”

Section: Methodsmentioning

confidence: 99%

“…:15 Mp 47-48 C (lit 13. 48-49 C); 1 H NMR (400 MHz, CDCl 3 , 20 C): 8.12 (d, J ¼ 8:4 Hz, 2H), 7.67 (d, J ¼ 8:4 Hz, 2H), 7.65-7.62 (m, 2H), 7.49-7.46 (m, 2H), 7.42-7.40 (m, 1H), 4.41 (q, J ¼ 7:2 Hz, 2H), 1.42 (t, J ¼ 7:2 Hz, 3H); 13 C NMR (150 MHz, CDCl 3 , 20 C):166.4, 145.4, 139.9, 129.9, 129.1, 128.8, 128.0, 127.1, 126.9, 60.8, 14.2; IR (KBr): 1710, 1606, 1277, 1115, 748 cm À1 .…”

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confidence: 99%

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Direct Conversion of Aromatic Ketones to Arenecarboxylic Esters via Carbon–Carbon Bond-Cleavage Reactions

Yin¹,

Gao²,

Wang³

et al. 2008

Bulletin of the Chemical Society of Japan

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Aromatic methyl ketones,-keto esters, and trifluoromethyl-1,3-diketones can be directly converted to arenecarboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.

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Quaternary Pyridinium Compounds

Shaw

1961

Chemistry of Heterocyclic Compounds: A Series of Monographs

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The Reaction of Ketones with Iodine and Pyridine

Cited by 19 publications

References 0 publications

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

Platinum(II) Complexes with π‐Conjugated, Naphthyl‐Substituted, Cyclometalated Ligands (RC^N^N): Structures and Photo‐ and Electroluminescence

Direct Conversion of Aromatic Ketones to Arenecarboxylic Esters via Carbon–Carbon Bond-Cleavage Reactions

Quaternary Pyridinium Compounds

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