Carbene reactions with pentafluorophenol

Brooke, Gerald M.; Cooper, Julian A.; Howard, Judith A. K.; Yufit, D. S.

doi:10.1016/s0022-1139(98)00120-1

Cited by 5 publications

(4 citation statements)

References 9 publications

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“…It is a colourless solid which melts at 146±147°C. NMR and mass spectra match well with recently published data [9].…”

Section: Resultssupporting

confidence: 87%

“…Probably, this reaction step is very similar to the recently published procedure starting from chloroform, sodium trichloroacetate and pentafluorophenol [9].…”

Section: Resultsmentioning

confidence: 60%

“…Tetrakis(pentafluorophenoxy)ethene has previously been described [9] and is the first example of a tetraphenoxy-substituted ethene. It is a colourless solid which melts at 146±147°C.…”

Section: Resultsmentioning

confidence: 99%

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The Reactions of Zn(CF3)Br · 2 CH3CN with Phenol, Pentafluorophenol, their Potassium and Ammonium Salts

Pasenok

Yagupolskii

Tyrra

et al. 1999

Z. anorg. allg. Chem.

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Triphenoxymethane, tris(pentafluorophenoxy)methane, phenyl(difluoromethyl)ethers, and tetrakis(pentafluorophenoxy)ethene were prepared via carbenoid reactions of Zn(CF3)Br · 2 CH3CN and the corresponding phenol or the potassium or ammonium salts in the presence of the auxiliary acid BF3 · O(CH3)2. The products were identified by their melting and boiling points and in part by their NMR and mass spectra as well as elemental analysis.

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“…It is a colourless solid which melts at 146±147°C. NMR and mass spectra match well with recently published data [9].…”

Section: Resultssupporting

confidence: 87%

“…Probably, this reaction step is very similar to the recently published procedure starting from chloroform, sodium trichloroacetate and pentafluorophenol [9].…”

Section: Resultsmentioning

confidence: 60%

See 1 more Smart Citation

The Reactions of Zn(CF3)Br · 2 CH3CN with Phenol, Pentafluorophenol, their Potassium and Ammonium Salts

Pasenok

Yagupolskii

Tyrra

et al. 1999

Z. anorg. allg. Chem.

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“…The closely related tetrakis(pentafluorophenoxy)ethane was formed in the reaction of pentafluorophenol with sodium trichloroacetate (which serves as the :CCl 2 carbene precursor). 24 Based on this literature precedent a plausible mechanism can be drawn (Scheme 7). The mechanism includes the initial formation of the :CF 2 carbene via the CF 3 anion, which itself is formed by displacement reaction from Ruppert's reagent by fluoride ions.…”

Section: Methodsmentioning

confidence: 99%

Syntheses and characterization of bis(trifluoromethyl)phosphino naphthalenes and acenaphthenes

et al. 2010

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Syntheses of heteroleptic 1,8-bis(phosphino)naphthalenes and 5,6-bis(phosphino)acenaphthenes were attempted using several synthetic strategies. Reaction of aryllithium with triphenylphosphite gave ArP(OPh)(2) (Ar = substituted naphthalene or acenaphthene), which was transformed into ArP(CF(3))(2), using a nucleophilic trifluoromethylation reaction with Me(3)SiCF(3)/CsF. The importance of the correct choice of solvent for the trifluoromethylation reactions is discussed. The incompatibility of ArP(CF(3))(2) with organolithium hampered the attachment of the second phosphine functionality to the organic backbone. Tetraphenoxyethylene was obtained in a small amount as a side product in the trifluoromethylation reaction. Selected new compounds were characterized by single-crystal X-ray diffraction.

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