Synthesis and reactions of 2-SF5-butadiene

Winter, R.; Gard, Gary L.

doi:10.1016/j.jfluchem.2007.03.008

Cited by 13 publications

(10 citation statements)

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“…Gard and Winter described the synthesis of both 3-pentafluorosulfur-3-sulfolene (8) and 4-pentafluorosulfur-2sulfolene (7) through the electrophilic addition of pentafluorosulfur bromide to 1 followed by dehydrobromination (Scheme 3). 21 Exposure of 3-sulfolene to pentafluorosulfur bromide with a sunlamp successfully afforded 3-bromo-4pentafluorosulfur-sulfolane (6) in a 67% yield. While elimination of hydrogen bromide with silver tosylate gave 7 as the major product, along with a trace of 8, the treatment of 6 with silver acetate provided a near-equimolar mixture of 2-sulfolene and 3-sulfolene SF 5 isomers.…”

Section: Scheme 2 Synthesis Of 3-(phenylthio)-3-sulfolenementioning

confidence: 99%

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3-Sulfolenes and Their Derivatives: Synthesis and Applications

Brant

Wulff

2015

Synthesis

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The diverse substitution patterns available to 3-sulfolenes have long made them useful for the preparation of multi-substituted 1,3-diene equivalents. More recently, the 3-sulfolene motif itself (or its reduced sulfolane congener) is finding increasing application as a structural element in the creation of molecules for biological applications. This review describes various methods to afford 3-sulfolene building blocks and their derivatives. Selected applications in synthetic and medicinal chemistry are also discussed. 1 Introduction 2 The Preparation of Monocyclic Sulfolene Building Blocks 2.1 Sulfolenes through Electrophilic Addition 2.1.1 Sulfolenes through Nucleophilic Addition to 4-Bromo-2-sulfolene 2.2 Sulfolenes through Oxidation of a Thiol Precursor 2.3 Sulfolenes through Noble Metal Catalysis 2.4 Sulfolenes through Deprotonation Followed by Alkylation 3 Synthesis of Bicyclic Sulfolenes and Their Derivatives 3.

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Section: Scheme 2 Synthesis Of 3-(phenylthio)-3-sulfolenementioning

confidence: 99%

“…3-Sulfolene 8 was ultimately provided in a 35% yield. 21 Compound 8 proved a useful in situ source of the corresponding 1,3-diene; for example, heating of 8 with maleic anhydride afforded the Diels-Alder adduct 9 in high yield.…”

Section: Scheme 2 Synthesis Of 3-(phenylthio)-3-sulfolenementioning

confidence: 99%

3-Sulfolenes and Their Derivatives: Synthesis and Applications

Brant

Wulff

2015

Synthesis

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“…3-SF 5 -4-Bromo sulfolane was obtained by addition of SF 5 Br to sulfol-3-ene (Scheme 21) [52]. This molecule was then used as an efficient precursor of 2-SF 5 -butadiene (see Section 3.2, Scheme 75).…”

Section: Scheme 20mentioning

confidence: 99%

“…A conceptually different approach to an SF 5 -alkene was reported by Winter and Gard who described the silicic acid promoted isomerisation 3-SF 5 -4-sulfolene to the corresponding 3-sulfolene (Scheme 44) [52].…”

Section: Scheme 43mentioning

confidence: 99%

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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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Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

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Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

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Synthesis and reactions of 2-SF5-butadiene

Cited by 13 publications

References 14 publications

3-Sulfolenes and Their Derivatives: Synthesis and Applications

3-Sulfolenes and Their Derivatives: Synthesis and Applications

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

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

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