Halogen displacement chemistry with silver and alkali metal salts: Preparation of SF5-esters, alcohols, aliphatic olefins, acids and an iodide

Winter, R.; Gard, Gary L.

doi:10.1016/j.jfluchem.2006.06.010

Cited by 14 publications

(7 citation statements)

References 13 publications

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“…However, it has been found that t-butyl tosylate, obtained by the silver salt method from (CH 3 ) 3 CCl, is an unstable compound and at %30 8C forms isobutylene and toluenesulfonic acid [8]. In our present paper, it was found that silver salt reactions with the SF 5 -containing alkyl halide (1) produce only olefinic products; no evidence was found for an ester-stage as was reported in earlier work [9].…”

Section: Resultssupporting

confidence: 65%

“…Reaction of sulfolene (4) with methyl acrylate preparation of (9) and (10) Sulfolene 4 (0.33 g, 1.3 mmol), benzene (10 ml), hydroquinone (14 mg) and methyl acrylate (0.39 g, 4.5 mmol) are heated in a 30 ml Carius tube in an oil bath at 125-135 8C for 4 h. The benzene is distilled away at atmospheric pressure and the residue was taken up in 2 ml of methylene chloride; this solution was passed through 2 g of Kieselgel, and after evaporation, 0.24 g of a colorless oil (65%) remained; an isomeric mixture of compounds (9) and (10).…”

Section: -Sf 5 -Anthraquinone (8)mentioning

confidence: 99%

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Synthesis and reactions of 2-SF5-butadiene

Winter¹,

Gard²

2007

Journal of Fluorine Chemistry

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Section: Resultssupporting

confidence: 65%

Section: -Sf 5 -Anthraquinone (8)mentioning

confidence: 99%

Synthesis and reactions of 2-SF5-butadiene

Winter¹,

Gard²

2007

Journal of Fluorine Chemistry

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“…Addition of SF 5 Cl to allyl acetate was subsequently described to occur efficiently [55]. Dimethyl itaconate was also successfully reacted with SF 5 Br affording the expected addition product in good yields (Scheme 25) [56].…”

Section: Scheme 22mentioning

confidence: 99%

“…Interestingly, treatment of 1-SF 5 -2-bromoethyl derivatives with AgOAc and acetic acid resulted in either elimination or in S N 2 reaction depending on the presence or not, respectively, of a bromine atom in -position to the SF 5 . (3-SF 5 -propyl)malonate was then prepared from the corresponding bromide and decarboxylated to give -SF 5 -pentanoic acid (Scheme 52) [56].…”

Section: Scheme 51mentioning

confidence: 99%

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

197

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The pentafluorosulfanyl group (SF5) is a highly stable chemical function which has been attracting a great deal of interest owing to its peculiar chemical, structural, physicochemical and biological properties. Progress in the area of SF5-compounds has been somewhat hindered by the lack of straightforward lab-scale synthetic methods for introducing the SF5-group into organic molecules. However, recent synthetic progress, the availability of some SF5-building blocks from commercial suppliers and the discovery of interesting properties of SF5-substituted molecules in materials science, biology and drug discovery are giving new momentum to research in this fascinating area of fluorine chemistry. Synthesis, reactivity and biological properties of SF5-substituted organic molecules are herein reviewed with an emphasis on the work published after year 2000. Object *Cover Letter or Page containing Author DetailsAll of the referees' suggestions have been accepted, with the only exception of Referee's 2 point 5 "Reactions of ArylSF5 systems should be divided into sections …electrophilc substitutions, nucleophilic substitutions, reactions of diazo systems,…" because in that section the chemistry is inherently heterogeneous and we feel that such a subclassification would be very challenging to achieve and would make less homogeneous the discussion of the topic. Molecolare, via Mancinelli 7, 20131 Milano, Italy Synthesis, reactivity and biological properties of SF 5 -substituted organic molecules are reviewed in this article, with an emphasis on the work published in the last decade. *Graphical Abstract -Synopsis Highlights We review the synthesis of SF 5 -compounds, with an emphasis on work published after year 2000.  We review the reactivity of SF 5 -substituted organic molecules.  We review the biological properties of SF 5 -substituted drug candidates. Aberdeen, Foresterhill, Aberdeen AB25 2ZD, Scotland, UK; e-mail: m.zanda@abdn.ac.uk b C.N.R.-Istituto di Chimica del Riconoscimento Molecolare, via Mancinelli 7, 20131 Milano, Italy AbstractThe pentafluorosulfanyl group (SF 5 ) is a highly stable chemical function which has been attracting a great deal of interest owing to its peculiar chemical, structural, physicochemical and biological properties. Progress in the area of SF 5 -compounds has been somewhat hindered by the lack of straightforward lab-scale synthetic methods for introducing the SF 5 -group into organic molecules. However, recent synthetic progress, the availability of some SF 5 -building blocks from commercial suppliers and the discovery of interesting properties of SF 5 -substituted molecules in materials science, biology and drug discovery are giving new momentum to research in this fascinating area of fluorine chemistry. Synthesis, reactivity and biological properties of SF 5 -substituted organic molecules are herein reviewed with an emphasis on the work published after year 2000.

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“…7 Winter and Gard reported the use of silver salts of various nucleophiles to avoid elimination and favor the substitution on (2-bromoethyl)pentafluorosulfane (Scheme 2, eq 3). 22 Given this precedent (even though only a brominated substrate was used), we wondered, in our case, if the use of silver additive could favor the cyclization over the elimination. Key optimization results are presented in Table Gard's conditions, we initially screened a range of silver salts in CH 3 CN at 80 °C (Table 1, entries 1−4).…”

mentioning

confidence: 98%

Silver-Promoted Synthesis of 5-[(Pentafluorosulfanyl)methyl]-2-oxazolines

2018

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The synthesis of 5-[(pentafluorosulfanyl)methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)propyl]amide to occur without elimination of the chlorine atom, a reaction pathway typically observed for β-chloro-SF5-alkyl compounds. The products, potentially valuable SF5-containing heterocycles, are obtained in up to 97% yield.

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Halogen displacement chemistry with silver and alkali metal salts: Preparation of SF5-esters, alcohols, aliphatic olefins, acids and an iodide

Cited by 14 publications

References 13 publications

Synthesis and reactions of 2-SF5-butadiene

Synthesis and reactions of 2-SF5-butadiene

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

Silver-Promoted Synthesis of 5-[(Pentafluorosulfanyl)methyl]-2-oxazolines

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