Vinylic halogen exchange reactions in 1,2-dihaloperfluorocycloalkenes

Soulen, Robert L.; Nakata, Bruce T.; Park, J.D.

doi:10.1016/s0022-1139(00)83217-0

Cited by 7 publications

(3 citation statements)

References 7 publications

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“…The infrared and n.m.r. spectra of the latter compound were as published (6). In addition the mass spectrum showed a parent ion at r~lle = 378 and intense peaks at 251 and 124 due to loss of iodine.…”

Section: ( B ) Tetrahydrojirrat~ Sohrtiotzmentioning

confidence: 86%

“…Initial reaction between the solvent and the carbonyl was apparent. Removal of the solvent followed by chromatography gave a very small amount of an orange oil whose infrared spectrum showed bands at 2100 ( The di-iodocyclobutenewas prepared following the published procedure by treating the dichloro compound with potassium iodide in dimethylformamide (6). In our hands the method gave a low yield (1.2%) of I-chloro-2-iodotetrafluorocyclobutene and a 14.5% yield of the di-iodo derivative.…”

Section: ( B ) Tetrahydrojirrat~ Sohrtiotzmentioning

confidence: 88%

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Fluoroalicyclic Derivatives of Cobalt Carbonyl

Cullen¹,

Jull²

1973

Can. J. Chem.

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Section: ( B ) Tetrahydrojirrat~ Sohrtiotzmentioning

confidence: 86%

Section: ( B ) Tetrahydrojirrat~ Sohrtiotzmentioning

confidence: 88%

Fluoroalicyclic Derivatives of Cobalt Carbonyl

Cullen¹,

Jull²

1973

Can. J. Chem.

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“…Dry and freshly prepared active Cu powder (2.54 g, 0.04 mol [34]; the precipitate was immediately washed with acetone and Et 2 O, allowing minimum exposure to air) and 1,2-diiodo-3,3,4,4-tetrafluorocyclobutene (1.85 g, 0.0049 mol [35]) were added to a sublimation apparatus under dry N 2 . The mixture was left overnight, then heated to 90 ± 938 in an oil bath for 24 h, and finally to 1358 for another 24 h. The dark red solid (0.65 g) collected from the cold finger was triturated in 5 ml of hot hexane, and filtered leaving 0.40 g of red crystals.…”

mentioning

confidence: 99%

Powerful Oxidizing Properties of a Planar [8]Annulene: Tetrakis(perfluorocyclobuta)cyclooctatetraene and Its Radical Anion

Gerson¹,

Huber²,

Merstetter³

et al. 1999

HCA

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The central eight‐membered ring of tetrakis(perfluorocyclobuta)cyclooctatetraene (1) is flat both in the crystal and in solution, but tetrakis(perfluorocyclopenta)cyclooctatetraene (2) assumes a tub shape similar to that of parent cyclooctatetraene. This sterically induced structural difference strongly affects the physical properties of compounds 1 and 2. The first and second reduction potentials of 1 in solution, +0.79 and +0.14 V vs. SCE, are considerably more positive than the corresponding values, +0.20 and −0.21 V, of 2. Accordingly, mere contact with Hg metal in N,N‐dimethylformamide converts 1 to an unusually stable radical anion 1.− that is persistent in air. The temperature‐independent coupling constant, aF=+0.320 mT, of the sixteen equivalent β‐19F‐nuclei in 1.− is much smaller than the expected value, and the g factor of 1.− is markedly lower than those generally found for structurally related radical anions. In contrast, the characteristic data for 2.−, generated from 2 with K metal in 1,2‐dimethoxyethane, comply with the expected data. The coupling constants aF=+0.976 and +0.935 mT, each of eight β‐19F‐nuclei in 2.−, average +0.951 mT upon raising the temperature from 220 to 260 K. The gas‐phase electron affinity of 1, A=3.4±0.2 eV, which was estimated from the reduction potential in solution and from charge‐transfer absorption spectra obtained from a series of methylated benzenes and naphthalenes, is among the highest known for neutral organic molecules.

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