173. Aromatic polyfluoro-compounds. Part VIII. Pentafluorobenzaldehyde and related pentafluorophenyl ketones and carboxylic acids

Barbour, A. K.; Buxton, Michael; Coe, Paul L.; Stephens, R.; Tatlow, J. C.

doi:10.1039/jr9610000808

Cited by 80 publications

(22 citation statements)

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“…The pentafluorobenzaldehyde in acetic anhydride, when treated with potassium acetate yielded 44% (E)-3-pentafluorophenyl-prop-2-ene acid (Scheme 26 [267]). In the conditions of Doebner condensation [267] with malonic acid in dry pyridine at temperature 100 8C during 1.5 h, it yielded 60% (E)-3-pentafluorophenyl-prop-2-ene acid.…”

Section: Chemical Reactions Of Pentafluorobenzaldehyde With Carbon Numentioning

confidence: 98%

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pažitný

Solčan

Végh

2009

Journal of Fluorine Chemistry

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Section: Chemical Reactions Of Pentafluorobenzaldehyde With Carbon Numentioning

confidence: 98%

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pažitný

Solčan

Végh

2009

Journal of Fluorine Chemistry

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“…Pentafluorobenzyl alcohol and bis(pentafluor0-pheny1)methanol were both prepared from pentafluorobenzaldehyde by Tatlow and coworkers (14), and tris(pentafluoropheny1)carbin01 (7) has been made through the reaction of pentafluorophenyl-lithium with decafluorobenzophenone by two groups of workers (15,16). Tamborski et al (17) prepared several tertiary arylalkyl perfluoroalcohols, including perfluoroup-dimethylbenzyl alcohol (S), from reactions of fluoroaryl lithium reagents with hexafluoroacetone.…”

Section: Pentafluorophenyl Alcoholsmentioning

confidence: 99%

“…The published method (14) for the preparation of octafluoroacetophenone, which was required for the synthesis of diol 9, makes use of the reaction between pentafluorophenyl Grignard reagents and lithium trifluoroacetate. This method gives only moderate yields (20-50%) and reactions between lithium reagents and acid chlorides were therefore investigated as possible routes to octafluoroacetophenone and other perfluoroarylketones.…”

Section: Esters Of Perfluoro Tertiary Alcoholsmentioning

confidence: 99%

“…Octafluoroacetophenone (12 g), prepared from lithium trifluoroacetate and pentafluorophenylmagnesium bromide (14), in 2-propanol(75 ml) with a few drops of hydrochloric acid, was irradiated (Hg lamp) for 5 days. Removal of volatile materials gave a yellow solid which was sublimed at 10O0/0.01 mm and recrystallized from ethanollhexane to give the diol9, m.p.…”

Section: Perjuoro(23-diphenyl-butane-23-diol) (Alcohol 9 )mentioning

confidence: 99%

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Studies on Fluorinated Vinylic and Aromatic Alcohols and Esters

Chang¹,

Price²,

Tomlinson³

et al. 1972

Can. J. Chem.

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Synthetic studies and pKa measurements are reported on a number of highly fluorinated tertiary alcohols and diols, namely (CF2CF)C(CF3)2OH, (CF2CF)2C(CF3)OH, (C6F5)C(CF3)2OH, (C6F5)2C(CF3)OH, (C6F5)3COH, (C6H5)C(CF3)2OH, [(CF3)2COH]2, and [(C6F5)C(CF3)OH]2. General agreement is found with earlier work reporting a correlation between pKa values and differences between free and H-bonded O—H stretching frequencies.The reaction of C6F5Li with the acyl halides CF3COCl and C6F5COCl in appropriate molar ratio gives the esters (C6F5)2C(CF3)OCOC6F5 and (C6F5)3COCOC6F5, respectively; this constitutes a useful preparative route to fully fluorinated esters.

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“…Methyl pentafluorophenyl ketone was prepared by the Grignard reaction o f acetyl chloride with pentafluoroohenvl mannesium bromide (18). A solution of the ketone i5.1 g) in 2-propanol (25 mi) in a quartz tube was degassed and irradiated with ultraviolet light for 7 days.…”

Section: 3-bis(pentaj7~rorophenyl) Butane-23-diolmentioning

confidence: 99%

Fluorinated Alkoxides. Part IX. The Resolution Of Perfluoro(2,3-diphenylbutane-2,3-diol) and its use in preparing Optically Active Complexes Of Ni²⁺ and Cu²⁺

Cripps¹,

Willis²

1975

Can. J. Chem.

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. Can. J. Chem. 53,817 (1975). Perfluoro(2,3-diphenylbutane-2,3-diol), CF3(C6F5)C(OH)C(OH)(C6F5)CF3, prepared by the reductive dimerization of C6F5COCF3, has been separated into meso-and DL-isomers and the latter resolved via its cinchonidine salt into optical enantiomers. The doubly ionized diol, PDBDZ-, acts as a dinegative, chelating, ligand, and neutral complexes of the form (PDBD)-MLz may be isolated, where L is a neutral nitrogen-or phosphorus-containing ligand and M = NiZ+ or C u z + . Use of the resolved diol enables optically active metal complexes to be prepared, and from their o.r.d.1c.d. spectra we assign an absolute configuration to the diol. The partially fluorinated diols CF3(C6H5)C(OH)C(OH)(C6H5)CF3 and CH3(C6F,)C(OH)-C(OH)(C6F5)CH3 have also been prepared from the appropriate ketones. The former, which appears to be exclusively the meso-isomer, has more limited chelating ability than the fully fluorinated analog, while the latter shows no ligand properties; these differences are ascribed to the reduced acidity resulting from the lower degree of fluorination.Nuclear magnetic resonance studies suggest hindered rotation of the C6F5 groups through steric interaction with CF3 groups in perfluoro(2,3-diphenylbutane-2,3-diol); an alternate explanation involving hydrogen bonding from the hydroxylic proton to aromatic fluorine atoms is considered less likely. C,F5)CH3. Le premier, qui semble Ctre exclusivernent I'isomere miso, a des propriktks chtlatantes plus limitees que son analogue completement fluore alors que le dernier ne prtsente aucune propriett comme ligand; on attribue ces differences a une acidit6 reduite resultant du degre plus bas de fluoration.Des etudes par resonance magnetique nuclkaire suggerent une rotation empCchCe des groupes C6F5 due a des interactions sttriques du groupe CF3 dans le perfluoro diphinyl-2,3 butanediol-2,3; on considere comme moins probable l'explication impliquant des liens hydrogene entre les protons hydroxyliques et les atomes de fluor du noyau aromatique.[Traduit par le journal]We have previously (1) reported the preparation of perfluoro(2,3-diphenylbutane-2,3-diol) C6F5C0CF3 (1) by the reductive dimerization of octafluoroacetophenone, and noted that the product appeared to contain more than one isomer. We now confirm this by the separation of the mesoisomer (la) and the DL-isomer (lb), followed by 'Presented in part at the 7th International Symposium on Fluorine Chemistry, Santa Cruz, California, July, 1973. Can. J. Chem. Downloaded from www.nrcresearchpress.com by 54.191.190.102 on 05/12/18For personal use only.

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173. Aromatic polyfluoro-compounds. Part VIII. Pentafluorobenzaldehyde and related pentafluorophenyl ketones and carboxylic acids

Cited by 80 publications

References 0 publications

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Studies on Fluorinated Vinylic and Aromatic Alcohols and Esters

Fluorinated Alkoxides. Part IX. The Resolution Of Perfluoro(2,3-diphenylbutane-2,3-diol) and its use in preparing Optically Active Complexes Of Ni²⁺ and Cu²⁺

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173. Aromatic polyfluoro-compounds. Part VIII. Pentafluorobenzaldehyde and related pentafluorophenyl ketones and carboxylic acids

Cited by 80 publications

References 0 publications

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Studies on Fluorinated Vinylic and Aromatic Alcohols and Esters

Fluorinated Alkoxides. Part IX. The Resolution Of Perfluoro(2,3-diphenylbutane-2,3-diol) and its use in preparing Optically Active Complexes Of Ni2+ and Cu2+

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Fluorinated Alkoxides. Part IX. The Resolution Of Perfluoro(2,3-diphenylbutane-2,3-diol) and its use in preparing Optically Active Complexes Of Ni²⁺ and Cu²⁺