Journal of Fluorine Chemistry

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Reactivity of perfluorohexyl iodide with N,N-disubstituted amides and esters in the presence of a metal couple and radical initiator

S. Benefice-Malouet, A. Commeyras

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 103-107

The reactivity of perfluorohexyl iodide with N,N-disubstituted amides or ethyl formate as solvents and reactants, in the presence of a zinc-copper metal couple and radical initiator, has been investigated. In each case, the corresponding perfluorinated carbonyl compounds, such as aldehydes, amides, ketones and esters, were obtained in good yield, thus proving the efficacy of this reaction. The influence...

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A high-yield synthesis of 3-carboethoxy-4-trifluoromethylfuran and some Diels-Alder reactions of this furoate with acetylenic dienophiles

Michael G. Barlow, Nadia N.E. Suliman, Anthony E. Tipping

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 59-69

The reaction of furan with ethyl 4,4,4-trifluorobut-2-ynoate (1) (1.2:1 molar ratio) in vacuo at 40 °C gives the 1:1 adduct oxanorbornadiene (3) (70%) and the 2:1 adduct (5) as the endo, exo (5a) (16%) and exo, exo (5b) (10%) isomers; at 20 °C, using an excess of ester 1, the yield of 1:1 adduct 3 is increased to 93%. Catalytic hydrogenation (Pd/C/Me ₂ CO) of 1:1 adduct3 with control of the...

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A simple one-pot synthesis of α-trifluoromethyl-substituted enamines by C-trifluoromethylation of dialkylamides with P(NEt ₂ ) ₃ /CF ₃ Br

Hans Bürger, Thomas Dittmar, Gottfried Pawelke

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 89-93

Dialkylamides of the general formula R ³ R ² NC(O)CH ₂ R ¹ , and Me--N--C(O)--CH ₂ --(CH ₂ ) _n --CH ₂ , n = 1-3, react with the reagent combination P(NEt ₂ ) ₃ /CF ₃ Br in the presence of BCl ₃ to give α-trifluoromethyl enamines R ³ R ² N--C(CF ₃ ) CHR ¹ , R ¹ H,...

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Fluorinated acetylenes. Part 14. Reaction of hexafluorobut-2-yne with 3-carboethoxyfuran and with cycloheptatriene

Michael G. Barlow, Nadia N.E. Suliman, Anthony E. Tipping

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 95-102

Reaction of 3-carboethoxyfuran (4) with hexafluorobut-2-yne (5) (1:2 molar ratio) at room temperature in dichloromethane afforded the Diels-Alder 1:1 adduct (3) (7%) and three 2:1 adducts formed by further addition of the furan 4 across the least substituted double bond of 1:1 adduct 3, i.e. the exo,endo- (8a) (39.5%), exo,exo- (9a) (24%) andexo,exo - (10a) (24%) isomers in which the two CO ₂...

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Asymmetric synthesis of fluorinated L-tyrosine and meta-L-tyrosines

Michel Monclus, Carine Masson, André Luxen

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 39-43

A convenient asymmetric synthesis of (2S)-2-amino-3-(2-fluoro-5-hydroxyphenyl) propanoic acid, (2S)-2-amino-3-(4-fluoro-3-hydroxyphenyl) propanoic acid and (2S)-2-amino-3-(2-fluoro-4-hydroxyphenyl) propanoic acid is described. Key steps include the synthesis of the benzyl bromides, the alkylation of the glycine enolate derivative ((S)-Boc-BMI) and the hydrolysis of the alkylated Boc-BMI.

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Titanium-catalyzed addition of perfluoroalkyl iodides to alkenes

Charles R. Davis, Donald J. Burton, Zhen-Yu Yang

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 135-140

Perfluoroalkyl iodides, in the presence of a catalytic amount of Ti ⁰ generated in situ, add to alkenes in dimethoxyethane solvent to afford 1-(n-perfluoroalkyl)-2-iodoalkanes in moderate to good yields. 1-Alkenes, 1-alkynes and alkenes containing bromo or ester substituents gave yields of the 1:1 addition adducts with n-perfluoroalkyl iodides. 1-Alkenes containing ketone or alcohol groups...

article

1,3,4-Oxadiazoles with SF ₅ -containing substituents

M.E. Sitzmann

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 31-38

1,3,4-Oxadiazoles containing a combination of SF ₅ -perfluoroalkyl, SF ₅ -alkyl, polynitroalkyl and perfluoroalkyl substituents have been synthesized by cyclization (dehydration) of the corresponding diacyl hydrazines. The properties of oxadiazoles with SF ₅ -perfluoroalkyl substituents are compared with those of similar oxadiazoles containing the corresponding perfluoroalkyl...

article

Study of the alkylation of chlorosilanes. Part III. Synthesis and reactivity of new fluorinated organolithium reagents

B. Boutevin, F. Guida-Pietrasanta, A. Ratsimihety, G. Caporiccio

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 53-57

The effect of the structure of the fluoroalkyl group R _F C ₂ H ₄ , where R _F =CF ₃ , C ₆ F ₁ ₃ and (CF ₃ ) ₂ CF, on the synthesis and reactivity of organolithium reagents R _F C ₂ H ₄ Li towards trimethylchlorosilane, (CH ₃ ) ₃ SiCl, and tris(fluoroalkyl)silanes, R ₁ R ₂ ...

article

Synthesis of 2H,2H-perfluoroalkyl and 2H-perfluoroalkenyl carboxylic acids and amides

Samuel Achilefu, Laurence Mansuy, Claude Selve, Sylvie Thiebaut

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 19-26

An efficient and convenient procedure for the synthesis of 2-perfluoroalkyl ethanoic acids by direct oxidation of 2-perfluoroalkyl ethanols with Jones' reagent (CrO ₃ /H ₂ SO ₄ ) is described. Treatment of the acids with aqueous sodium hydroxide gave 3-perfluoroalkyl, 3-fluoro-2,3-propenyl carboxylic acids which may be used for the preparation of the corresponding chlorides...

article

Structural determination of chlorotrifluoroethylene dimers by ¹ ³ C- ¹ ⁹ F INEPT NMR

S. Yonemori, Y. Jitsugiri, M. Noshiro

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 27-29

The ¹ ³ C- ¹ ⁹ F INEPT NMR method has been applied to determine the chemical structures of the dimers of chlorotrifluoroethylene synthesized in sulfuryl chloride. These have been identified as a mixture of 1,2,4,4-tetrachlorohexafluorobutane and 1,1,4,4-tetrachlorohexafluorobutane.

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Semi-empirical molecular orbital studies of monofluorination reactions: reaction of hydrofluorocarbons over cobalt trifluoride

Shigeru Kurosawa, Akira Sekiya, Motonari Shibakami, Masanori Tamura, more

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 49-52

Theoretical studies of monofluorination reactions for hydrofluorocarbons (HFCs) over CoF ₃ have been performed by semi-empirical molecular orbital calculations. Heats of formation of intermediates such as cations or radicals have been calculated. The results are consistent with the experimental regioselectivity for the monofluorination of HFCs (C ₂ -C ₄ ) over CoF ₃ ...

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Free-radical addition of 2-(perfluoroalkyl)ethanethiols to alkenes, alkadienes, cycloalkenes, alkynes and vinyl monomers

Neal O. Brace

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 145

article

Reactions of CF ₃ SCl with amines and the formation of trifluoromethylthio-substituted enamines

Anna Kolasa, Max Lieb

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 45-47

The formation of bis-β,β-(CF ₃ S)-substituted enamines depends on the molar ratio of the starting materials. In this way, the yield of 1,1-bis(trifluoromethylthio)-2-(N,N-diethylamino)ethene was improved. The influence of amine structure on the formation of enamines is discussed.

article

Facile nucleophilic addition of thiols to 1,1-difluoroallene: a convenient approach to γ,γ-difluoroallyl sulphides

Yuan-yao Xu, Fu-qiang Jin, Wei-yuan Huang

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 5-6

In the presence of base, nucleophilic additions of thiols to 1,1-difluoroallene occur readily, yielding γ,γ-difluoroallyl sulphides in high yield.

article

Phenylbis(fluorosulfonyl)- and phenylbis(trifluoromethylsulfonyl)-methyliodonium triflates

I.I. Maletina, V.V. Orda, Yu.L. Yagupolskii

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 85-88

Phenyliodonium bis(fluorosulfonyl)methylide (I) and phenyliodonium bis(trifluoromethylsulfonyl)methylide (II) are converted to triflates of phenylbis(fluorosulfonyl)- (III) and phenylbis(trifluoromethylsulfonyl)-methyliodonium (IV), respectively, by the addition of equimolar amounts of trifluoromethanesulfonic acid in CH ₂ Cl ₂ . The existence of these triflates has been confirmed...

article

Solvent effects in the fluorination of aromatic molecules with F-TEDA-BF ₄

Marko Zupan, Jernej Iskra, Stojan Stavber

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 7-8

The type of functionalization of an aromatic molecule achieved with 1-chloromethyl-4-fluoro-1,4-diazobicyclo-(2,2,2)octane bis-tetrafluoroborate, F-TEDA-BF ₄ , in trifluoroacetic acid depends on its structure: naphthalene and phenanthrene gave fluorinated products, anthracene gave the trifluoroacetate, while an addition process occurred with 9-methoxy-phenanthrene in methanol, and an addition-elimination...

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Semi-empirical calculations on bis-halomethyl sulfides. A comparison of the structures and other parameters by MNDO, AM1 and PM3 methods

R.A. Taccone, O. Salinovich

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 9-17

Semi-empirical (MNDO, AM1 and PM3) calculations of geometry, heats of formation, ionization potential and dipole moments have been made of bis-halomethyl sulfides of the type R ¹ SR ³ (where R ¹ = CH ₃ or CF ₃ and R ³ = CH ₃ , CH ₂ Cl, CHCl ₂ , CCl ₃ , CFCl ₂ , CF ₂ Cl and CF ₃ ). Because of the...

article

Mise en evidence d'une reactivite specifique des trifluoromethylcetones vis-a-vis du bromure d'allylmagnesium

Caroline Felix, André Laurent, Pierre Mison

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 71-82

We wish to report on an unusual reactivity of allylmagnesium bromide. This Grignard reagent acts as a reducing agent towards trifluoromethylated ketones. A single electron transfer is suggested to explain the reductive process. By using an excess of allylmagnesium bromide, an exclusive addition reaction is obtained. The stereochemistry of both addition and reduction reactions is discussed.

article

Fluorinated acetylenes. Part 15 . The reaction of ethyl 4,4,4-trifluorobut-2-ynoate with dienes and cycloheptatriene

Michael G. Barlow, Nadia N.E. Suliman, Anthony E. Tipping

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 109-119

Thermal reaction of the acetylenic ester CF ₃ C CCO ₂ Et (1) with cyclopentadiene (4), buta-1,3-diene (5) and 1,4-diphenylbuta-1,3-diene (6) gave the corresponding Diels-Alder 1:1 cycloadducts 10, 11 and 12, respectively in high yield (73%-97%). With norbornadiene (7), the homo Diels-Alder adduct (13) was formed. The reaction with 3-carboethoxyfuran gave a mixture (55%) of the isomeric...

article

Potassium dihydrogen trifluoride: a novel fluorinating reagent for ring-opening of expoxides

Masanori Tamura, Motonari Shibakami, Takashi Arimura, Shigeru Kurosawa, more

Journal of Fluorine Chemistry > 1995 > 70 > 1 > 1-3

It has been found that potassium dihydrogen trifluoride is an efficient and easy-to-handle solid reagent for the ring-opening reaction of epoxides giving fluorohydrins regio- and stereo-selectively. The reaction proceeds via cis-addition of HF to the epoxide.

INFONA - science communication portal

Journal of Fluorine Chemistry

Reactivity of perfluorohexyl iodide with N,N-disubstituted amides and esters in the presence of a metal couple and radical initiator

A high-yield synthesis of 3-carboethoxy-4-trifluoromethylfuran and some Diels-Alder reactions of this furoate with acetylenic dienophiles

A simple one-pot synthesis of α-trifluoromethyl-substituted enamines by C-trifluoromethylation of dialkylamides with P(NEt ₂ ) ₃ /CF ₃ Br

Fluorinated acetylenes. Part 14. Reaction of hexafluorobut-2-yne with 3-carboethoxyfuran and with cycloheptatriene

Asymmetric synthesis of fluorinated L-tyrosine and meta-L-tyrosines

Titanium-catalyzed addition of perfluoroalkyl iodides to alkenes

1,3,4-Oxadiazoles with SF ₅ -containing substituents

Study of the alkylation of chlorosilanes. Part III. Synthesis and reactivity of new fluorinated organolithium reagents

Synthesis of 2H,2H-perfluoroalkyl and 2H-perfluoroalkenyl carboxylic acids and amides

Structural determination of chlorotrifluoroethylene dimers by ¹ ³ C- ¹ ⁹ F INEPT NMR

Semi-empirical molecular orbital studies of monofluorination reactions: reaction of hydrofluorocarbons over cobalt trifluoride

Free-radical addition of 2-(perfluoroalkyl)ethanethiols to alkenes, alkadienes, cycloalkenes, alkynes and vinyl monomers

Reactions of CF ₃ SCl with amines and the formation of trifluoromethylthio-substituted enamines

Facile nucleophilic addition of thiols to 1,1-difluoroallene: a convenient approach to γ,γ-difluoroallyl sulphides

Phenylbis(fluorosulfonyl)- and phenylbis(trifluoromethylsulfonyl)-methyliodonium triflates

Solvent effects in the fluorination of aromatic molecules with F-TEDA-BF ₄

Semi-empirical calculations on bis-halomethyl sulfides. A comparison of the structures and other parameters by MNDO, AM1 and PM3 methods

Mise en evidence d'une reactivite specifique des trifluoromethylcetones vis-a-vis du bromure d'allylmagnesium

Fluorinated acetylenes. Part 15 . The reaction of ethyl 4,4,4-trifluorobut-2-ynoate with dienes and cycloheptatriene

Potassium dihydrogen trifluoride: a novel fluorinating reagent for ring-opening of expoxides

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