The Chemistry Of Perchlorocyclopentenes And Cyclopentadienes

Ungnade, Herbert E.; McBee, E. T.

doi:10.1021/cr50020a003

Cited by 78 publications

(22 citation statements)

References 83 publications

(280 reference statements)

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“…THE CHEMISTRY of hexachlorocyclopentadiene has been reviewed (2,3 ) . Of particular interest have been the various products from the Diels-Alder reaction with unsaturated dicarboxylic acids or their anhydrides.…”

Section: Literature Citedmentioning

confidence: 99%

Synthesis of 1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,-8,8a-octahydro-1,4-methanonaphthalene-6,7-dicarboxylic acid and ester derivatives

Roberts¹,

Haigh²,

Rathsack³

1967

J. Chem. Eng. Data

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S-O. 'Analyzed by Galbraith Laboratories, Knoxville, Tenn. 'Not enough for NMR analysis.analysis by NMR indicated a mixture of 85% 1,2,2,2-tetrachloroethanesulfenyl chloride and 15% of the 1,1,2,2-tetrachloroethyl isomer). Water was then added to the mixture and the light yellow organic product separated. The aliphatic compounds were diluted with ether and dried over sodium sulfate before chromatographing. The aromatic compounds, which did not crystallize from the oil, were handled similarly.The compounds, which were purified by thin-layer chromatography, were applied in about 5% ether solution to plates coated to a thickness of 250 microns with silica gel GF 254 (Merck) containing a fluorescent indicator, and were developed in benzene, or benzene-petroleum ether (30 to 60°C .)-chloroform, 8:8:1 by volume.The NMR data were obtained on a Varían DP-60 nuclear magnetic resonance spectrometer. Chemical shifts were determined by side bands applied with an audio-oscillator for which the frequency is continuously monitored by an electronic counter. The samples were run in a concentration of 20 to 40% by volume in carbon tetrachloride at a temperature of approximately 33°C.The infrared spectra were obtained on a Beckman IR-4 spectrophotometer using sodium chloride optics. The liquid samples were run neat and the solids in Nujol mulls.

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Section: Literature Citedmentioning

confidence: 99%

Synthesis of 1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,-8,8a-octahydro-1,4-methanonaphthalene-6,7-dicarboxylic acid and ester derivatives

Roberts¹,

Haigh²,

Rathsack³

1967

J. Chem. Eng. Data

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“…Monoadducts of various dienes with 1,4‐benzoquinone are usually formed much easier than the subsequent bisadducts. It was noted that the reaction rates of 1,4‐benzoquinone with dienes are low, and the reaction products are thermally unstable 9–12 . However, quantitative kinetic data for such reactions are very limited, and the enthalpies of reaction are also unknown.…”

Section: Introductionmentioning

confidence: 99%

“…It was noted that the reaction rates of 1,4benzoquinone with dienes are low, and the reaction products are thermally unstable. [9][10][11][12] However, quantitative kinetic data for such reactions are very limited, and the enthalpies of reaction are also unknown. A significant increase in activity was observed for 2,3-dicyano-1,4-benzoquinone (2) in the reaction of [2 +2 +2 ]-cycloaddition with quadricyclane (6).…”

Section: Introductionmentioning

confidence: 99%

Study of all stages of the Diels–Alder reaction of cyclopentadiene with 2,3‐dicyano‐1,4‐benzoquinone and monoadducts: Kinetics, thermochemistry, and high pressure effect

Kolesnikova

Kornilov

Gubaidullin

et al. 2020

Int J of Chemical Kinetics

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The kinetic parameters and enthalpies of the Diels–Alder reactions between cyclopentadiene and 2,3‐dicyano‐1,4‐benzoquinone leading to the formation of two different monoadducts and bisadduct were determined. The stability of adducts is compared. Monoadduct appears to be thermodynamically more stable than the bisadduct. Comparison with the other Diels–Alder reactions studied previously allows us to conclude that the heat effects upon formation of the considered Diels–Alder adducts are the lowest in comparison with all the studied dienophiles.

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“…C-56 is a very reactive organic reagent. Because of its conjugated diene structure and chlorine substituents, it undergoes substitution, addition and Diels-Alder reactions to form acids, esters, ketones, quinones, nitriles and various dimerized hydrocarbons [3,4]. C-56 is very volatile; it has a vapor pressure of 0.1 torr at 25°C [5] and is photoreactive in sunlight, having a near-surface half-life in aquatic systems of less than 10 min [6].…”

Section: Introductionmentioning

confidence: 99%

Products of Hexachlorocyclopentadiene (C-56) in Aqueous Solution

Chou¹,

Griffin²,

Chou³

et al. 1987

Environ Toxicol Chem

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The photodegradation and degradation products of hexachlorocyclopentadiene (C-56) in aqueous solutions were studied in the laboratory. In each case, the half-life of C-56 was less than 4 min when exposed to sunlight. At least eight degradation products were positively or tentatively identified: 2,3,4,4,5-Pentachloro-2-cyclopentenone, hexachloro-2-cyclopentenone and hexachloro-3-cyclopentenone were the primary photodegradation products, and pentachlorocis-2,4-pentadienoic acid, Zand E-pentachlorobutadiene and tetrachlorobutyne were the secondary degradation products. Dissociation of the primary photolysis products may proceed through corresponding pentadienoic acids to form smaller molecular weight compounds such as pentachlorobutadiene isomers and tetrachlorobutyne. In addition, dimerization of 2,3,4,4,5-pentachloro-2-cyclopentenone to form higher molecular weight compounds such as hexachloroindenone may present a minor route of degradation. The results also indicate that C-56 is highly photoreactive and suggest a possible pathway for the compound's transformation in the environment R hen exposed to sunlight.

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The Chemistry Of Perchlorocyclopentenes And Cyclopentadienes

Cited by 78 publications

References 83 publications

Synthesis of 1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,-8,8a-octahydro-1,4-methanonaphthalene-6,7-dicarboxylic acid and ester derivatives

Synthesis of 1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,-8,8a-octahydro-1,4-methanonaphthalene-6,7-dicarboxylic acid and ester derivatives

Study of all stages of the Diels–Alder reaction of cyclopentadiene with 2,3‐dicyano‐1,4‐benzoquinone and monoadducts: Kinetics, thermochemistry, and high pressure effect

Products of Hexachlorocyclopentadiene (C-56) in Aqueous Solution

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