Skip to main content
Disciplines
Automotive Business IT + Informatics Construction + Real Estate Electrical Engineering + Electronics Energy + Sustainability Insurance + Risk Finance + Banking Management + Leadership Marketing + Sales Mechanical Engineering + Materials
Events
DE
EN
Books
Journals
Topic Page
Marketing
Start single access now
Access for companies
EXTENDED SEARCH
Log in
Top
Published in:
Aliphatic [18F]Fluorination Chemistry for Positron Emission Tomography Read chapter Read first chapter

2020 | OriginalPaper | Chapter

SF4 Deoxofluorination

Authors : Mingyou Hu, Jinbo Hu

Published in: Fluorination

Publisher: Springer Singapore

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Excerpt

Sulfur tetrafluoride (SF4) is a gas at ambient temperature, mp −121 °C and bp −38 °C [1]. The first unequivocal synthesis of SF4 was reported in 1950, by electrical decomposition of trifluoromethylsulfur pentafluoride (CF3SF5) [2]. Later, a practical synthesis of SF4 was developed by heating sulfur dichloride with sodium fluoride in acetonitrile at 50–70 °C in conventional glass equipment (Eq. 1). Volatile SF4 was collected in a cold trap [3].
https://static-content.springer.com/image/prt%3A978-981-10-3896-9%2F11/MediaObjects/978-981-10-3896-9_11_Part_Equ1-54_HTML.png
(1)
…

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

inform now
previous chapter SelectFluor Radical Fluorination for Preparing Alkyl Fluorides
next chapter Silver-Mediated Fluorination for Preparing Aryl Fluorides
Literature
1.
Brown F, Robinson PL (1955) Preparation and some physical properties of sulfur tetrafluoride. J Chem Soc (London) 1955: 3147–3151.
2.
Silvey GA, Cady GH (1950) Trifluoromethylsulfur pentafluoride. J Am Chem Soc 72: 3624–3626.
3.
Tullock CW, Fawcett FS, Smith WC, Coffman DD (1960) The chemistry of sulfur tetrafluoride. I. The synthesis of sulfur tetrafluoride J Am Chem Soc 82:539–542.
4.
Smith WC (1962) The Chemistry of sulfur tetrafluoride. Angew Chem Int Ed 1: 467–475.
5.
Hasek WR, Smith WC, Engelhardt VA (1960) The chemistry of sulfur tetrafluoride. II. The fluorination of organic carbonyl compounds. J Am Chem Soc 82:543–551.
6.
Wang CLJ (2004) Sulfur tetrafluoride. e-EROS Encyclopedia of Reagents for Organic Synthesis.
7.
Boswell GA, Jr, Ripka WC, Scribner RM, Tullock CW (1974) Fluorination by Sulfur Tetrafluoride. Org React 21:1–124.
8.
Wang CLJ (1985) Fluorination by sulfur tetrafluoride. Org React 34:319–400.
9.
(a) Beaulieu F, Beauregard LP, Courchesne G, Couturier M, LaFlamme F, L’Heureux A (2009) Aminodifluorosulfinium tetrafluoroborate salts as stable and crystalline deoxofluorinating reagents. Org Lett 11: 5050. (b) L’Heureux A, Beaulieu F, Bennett C, Bill DR, Clayton S, LaFlamme F, Mirmehrabi M, Tadayon S, Tovell D, Couturier M (2010) Aminodifluorosulfinium salts: Selective fluorination reagents with enhanced thermal stability and ease of handling. J Org Chem 75:3401.
10.
Burmakov AI, Khassanein SM, Kunshenko BV, Alekseeva LA, Yagupol’skii LM (1986) Interaction of hydroxy and carbonyl- compounds with sulfur tetrafluoride. 16. Reaction of vicinal diatomic alcohols with SF4. J Org Chem USSR (Engl Transl) 22:1146–1149.
11.
Khassanein SM, Burmakov AI, Bloshchitsa FA, Yagupol’skii LM (1988) Interaction of hydroxycarbonyl and carbonyl-compounds with sulfur tetrachloride. 20. Glycol reaction with SF4. J Org Chem USSR (Engl Transl) 24:1473–1478.
12.
Kollonitsch J, Marburg S, Perkins L (1975) Selective fluorination of hydroxy amines and hydroxy amino acids with sulfur tetrafluoride in liquid hydrogen fluoride. J Org Chem 40:3808–3809.
13.
Edwards JA, Holton PG, Orr JC, Ibanez LC, Necoechea E, De La Roz A, Segovia E, Urquiza R, Bowers A (1963) Steroids. CCVIII. Ring A modified hormone analogs. Part IV. 2-Chloro and 2-halomethyl-Δ2-androstenes. J Med Chem 6:174–177.PubMed
14.
Martin DG, Kagan F (1962) The reaction of sulfur tetrafluoride with steroids. J Org Chem 27:3164–3168.
15.
Lukmanov VG, Alekseev LA, Burmakov AL, Yagupol’skii LM (1973) Fluorination of aromatic carboxylic-acids by sulfur tetrafluoride. 8. Synthesis of vicinal polytrifluoromethyl benzenes. J Org Chem USSR (Engl Transl) 9:1046–1051.
16.
Kagan F, Martin DG (1967) Process for the preparation of difluorosteroids. US Pat 3297728.
17.
Raasch, MS (1962) The chemistry of sulfur tetrafluoride. IX. Reaction with amino acids in hydrogen fluoride. J Org Chem 27:1406–1409.
18.
Fialkov YA, Moklyachuk LI, Kremlev MM, Yagupol’skii LM (1980) Fluorination of aromatic carboxylic acids by sulfur tetrafluoride. 13. Fluorination of methylester of benzoic acid and its substitutes in hydrogen fluoride. J Org Chem USSR (Engl Transl) 16:1269–1272.
19.
De Pasquale RJ (1978) An approach to the synthesis of perfluoro tertiary amines. J Org Chem 43:1727–1729.
20.
Yagupol’skii LM, Golikov VI, Alekseev LA, Aleksand AM (1971) Oxidrane reactions with sulfur tetrafluoride. 1. Monophenyloxiranes and 1,2-diphenyloxiranes. J Org Chem USSR (Engl Transl) 7:737–740.
21.
Yagupol’skii LM, Kondratenko NV, Popov VI (1976) Aromatic fluorides of pentavalent antimony. J Gen Chem USSR (Engl Transl) 46:618–621.
22.
Messina PA, Mange KC, Middleton WJ (1989) Aminosulfur trifluorides: Relative thermal stability. J Fluorine Chem 42:137–143.
23.
Hudlicky M (1988) Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes. Org React 35:513–637.
24.
Li SH, Wu P, Moses JE, Sharpless KB (2017) Multidimensional SuFEx click chemistry: Sequential sulfur(VI) fluoride exchange connections of diverse modules launched from an SOF4 hub. Angew Chem Int Ed 56:2903–2908.
25.
Gao B, Li S, Wu P, Moses JE, Sharpless KB (2018) SuFEx chemistry of thionyl tetrafluoride (SOF4) with organolithium nucleophiles: Synthesis of sulfonimidoyl fluorides, sulfoximines, sulfonimidamides, and sulfonimidates. Angew Chem Int Ed 57:1939–1943.
Metadata
Title
SF4 Deoxofluorination
Authors
Mingyou Hu
Jinbo Hu
Copyright Year
2020
Publisher
Springer Singapore
Book
Fluorination

Print ISBN: 978-981-10-3895-2

Electronic ISBN: 978-981-10-3896-9

Copyright Year: 2020

DOI
https://doi.org/10.1007/978-981-10-3896-9_54

Premium Partners

    Image Credits