Anionic derivatives of pentafluoro-λ6-sulfanyl (fluorosulfonyl) acetic acid esters

Winter, R.; Gard, Gary L.; Mews, R.; Noltemeyer, M.

doi:10.1016/s0022-1139(00)80025-1

Cited by 14 publications

(7 citation statements)

References 16 publications

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“…The O3···O4 intermolecular distance is 2.688(5) Å, comparable to that found in other fluorinated acetic acids in the solid phase. − The substituents on sulfur are staggered with respect to those on C1: the F1−S−C1−C2 dihedral angle is 60.1(4)°. The bond lengths and angles in the C−SO 2 F system are comparable to those in other compounds, − except that the SO bond lengths are among the shortest reported so far (1.381 and 1.393 Å compared to 1.389−1.446 Å, average 1.412 Å), and the F1−S−C1 bond angle is less than that in the other compounds (99.1° compared to 99.9−111.0°, average 103.6°). The latter is due to a conformation induced by hydrogen bonding to the sulfonyl oxygens, as described below.…”

Section: Resultssupporting

confidence: 72%

“…Since the title compound, 1 , has a higher melting point (50−51 °C) than that of the related compounds FSO 2 CH 2 COOH (37 °C) and FSO 2 CF 2 COOH (liquid, bp 153 °C) and since relatively few crystal structures of compounds containing the −SO 2 F group attached to carbon are known, − we decided to investigate the crystalline nature of 1 . Although it was first prepared in 1961, only its melting point was reported, and we therefore undertook further characterization of this compound.…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structure of (Fluorosulfonyl)fluoroacetic Acid: A Novel Four-Center Hydrogen-Bond System Involving a C−H Donor

1996

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The crystal structure of FSO 2 CFHCOOH has been determined by a single-crystal X-ray study. The crystals are monoclinic, of space group P2 1 /c, and have the following cell parameters: a ) 5.0164(6) Å, b ) 9.658(2) Å, c ) 11.061(2) Å, ) 90.54(1)°, Z ) 4. The carboxyl groups of the molecules form the usual hydrogen-bonded, centrosymmetric dimers, but each molecule also interacts with three other neighboring molecules by hydrogen bonds from the methine hydrogen to two sulfonyl oxygens and to a carbonyl oxygen, making a four-center system. The extensive network of hydrogen bonding in this material appears to be responsible for its existence as a solid.

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Section: Resultssupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

Crystal Structure of (Fluorosulfonyl)fluoroacetic Acid: A Novel Four-Center Hydrogen-Bond System Involving a C−H Donor

1996

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“…This finding built on extensive previous work dedicated to the preparation of SF 5 -substituted -sultones and their conversion into fluorosulfonyl derivatives [90] (for a review see [91]). …”

Section: Scheme 57mentioning

confidence: 91%

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

Zanda

Altomonte

2012

Journal of Fluorine Chemistry

198

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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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“…Esterification with alcohols in refluxing concentrated sulfuric acid produced the corresponding esters 198 in good yields greater than 80% . Treatment of ester 203 with amine or alkoxide bases afforded ester salt 204 , with the negative charge in the α position to the SF 5 and CO 2 R groups in yields greater than 50% . Synthesis of 1,3,4-oxadiazoles containing the SF 5 group in a substituent bonded to a carbon atom in the ring was accomplished in 50–94% yield by dehydration of the corresponding diacylhydrazines using either PCl 5 or POCl 3 (Scheme ) …”

Section: Chemistry Of Aliphatic Sf5 Compoundsmentioning

confidence: 99%

“…One of the more versatile SF 5 -substituted unsaturated compounds is SF 5 -ketene. Ketenes have been used to prepare a variety of organic compounds ranging from carboxylic acid derivatives, ,,, ethers, and alkylidenesulfur fluorides. , Additionally, SF 5 -ketene has been observed to dimerize upon heating ,,, and in the presence of a metal fluoride (e.g., KF or CsF) polymerizes to form a rubbery solid. , Scheme illustrates the various reactions of SF 5 ketenes.…”

Section: Chemistry Of Aliphatic Sf5 Compoundsmentioning

confidence: 99%

Preparation and Utility of Organic Pentafluorosulfanyl-Containing Compounds

2014

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Scheme 113. Preparation of SF 5 -Containing Arylboronic Acids and Use in Conia−Ene Cyclizations a a Reagents and conditions: (a) i-PrMgBr (1.2 equiv), B(OMe) 3 THF, −78 to 25 °C (65%); (b) 429, PhMe (3−73%). Scheme 114. Preparation of SF 5 -Containing Binaphthyl Compounds a a Reagents and conditions: (a) 428, Pd(PPh 3 ) 4 (10%), K 2 CO 3 , DMF; (b) BBr 3 (75%); (c) POCl 3 ; (d) H 2 O. Scheme 115. Asymmetric Protonation via SF 5 -Containing Acid 436 a a Reagents and conditions: (a) 436 (catalytic).

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Anionic derivatives of pentafluoro-λ6-sulfanyl (fluorosulfonyl) acetic acid esters

Cited by 14 publications

References 16 publications

Crystal Structure of (Fluorosulfonyl)fluoroacetic Acid: A Novel Four-Center Hydrogen-Bond System Involving a C−H Donor

Crystal Structure of (Fluorosulfonyl)fluoroacetic Acid: A Novel Four-Center Hydrogen-Bond System Involving a C−H Donor

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

Preparation and Utility of Organic Pentafluorosulfanyl-Containing Compounds

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