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Aliphatic [18F]Fluorination Chemistry for Positron Emission Tomography Read chapter Read first chapter

2020 | OriginalPaper | Chapter

Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) Deoxofluorination

Authors : Lingchun Li, Jinbo Hu

Published in: Fluorination

Publisher: Springer Singapore

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Excerpt

Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) was first introduced by Carpino and El-Faham in 1995, which is a nonhygroscopic white crystalline salt stable to handling under ordinary conditions [1]. Differential scanning calorimetry (DSC) analysis of TFFH revealed a decomposition temperature (Tmax) at 370 °C with an exothermic heat (–ΔH) of 146 J/g [2]. Comparing with the -ΔH values of XtalFluor-E (1260 J/g) at Tmax = 205 °C and XtalFluor-M (773 J/g) at Tmax = 243 °C [3], TFFH is significantly more stable and safe. Not surprisingly, TFFH is an easily handled reagent that possesses long shelf life and has found many applications in organic synthesis [4]. …

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previous chapter Tetrafluoroborate Salt Fluorination for Preparing Alkyl Fluorides
next chapter Transition Metal-Mediated Fluorination with Electrophilic/Nucleophilic Fluorinating Agents
Literature
1.
Carpino, L. A.; El-Faham, A. J. Am. Chem. Soc.1995, 117, 5401–5402.
2.
Bellavance, G.; Dubé, P.; Nguyen, B. Synlett2012, 23, 569–574.
3.
L’Heureux, A.; Beaulieu, F.; Bennett, C.; Bill, D. R.; Clayton, S.; LaFlamme, F.; Mirmehrabi, M.; Tadayon, S.; Tovell, D.; Couturier, M. J. Org. Chem.2010, 75, 3401–3411.PubMedPubMedCentral
4.
El-Faham, A.; Khattab, S. N. Synlett2009, 886–904.
5.
Pittelkow, M.; Kamounah, F. S.; Boas, U.; Pedersen, B.; Christensen, J. B. Synthesis2004, 2485–2492.
6.
El-Fahm, A.; Abdul-Ghani, M. Org. Prep. Proced. Int.2003, 35, 369–374.
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Metadata
Title
Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) Deoxofluorination
Authors
Lingchun Li
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_50

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