(Re)Investigation of the reactivity of uranium hexafluoride toward several organic functions at room temperature

Roy, Olivier; Marquet, B.; Alric, J. P.; Alex, Jourdan; Morel, Bertrand; Langlois, Bernard R.; Billard, Thierry

doi:10.1016/j.jfluchem.2014.06.007

Cited by 12 publications

(5 citation statements)

References 17 publications

(47 reference statements)

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“…In 2014, Langlois, Billard and co-workers developed the deoxofluorination of carboxylic acids using UF 6 (Scheme 427). 549 3.2.4.2. Fluorination of Acyl Halides.…”

Section: Scheme 387mentioning

confidence: 99%

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Monofluorination of Organic Compounds: 10 Years of Innovation

et al. 2015

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“…In 2014, Langlois, Billard and co-workers developed the deoxofluorination of carboxylic acids using UF 6 (Scheme 427). 549 3.2.4.2. Fluorination of Acyl Halides.…”

Section: Scheme 387mentioning

confidence: 99%

“…It is worth noting that aldehydes can also be transformed into acyl fluorides using UF 6 549 or by photocatalysis 94 (see section 3.1.1.5.5).…”

Section: Scheme 387mentioning

confidence: 99%

Monofluorination of Organic Compounds: 10 Years of Innovation

et al. 2015

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“…More puzzlingly, treatment of diethylmalonic acid with dicyclohexylcarbodiimide produced material with IR bands of medium intensity at 1900 and 1980 cm –1 , with the former slightly more intense, and assigned as 1 (R, R′ = C 2 H 5 ), but not further characterized, not even in the full paper . More recently, it was claimed that dehydration of dimethylmalonic acid with UF 6 produced dimethylmalonic anhydride ( 1 , R, R′ = CH 3 ), as characterized by GC but without any IR evidence . In summary, monomeric malonic anhydrides were elusive.…”

Section: Historymentioning

confidence: 99%

“…14 More recently, it was claimed that dehydration of dimethylmalonic acid with UF 6 produced dimethylmalonic anhydride (1, R, R′ = CH 3 ), as characterized by GC but without any IR evidence. 15 In summary, monomeric malonic anhydrides were elusive.…”

Section: ■ Historymentioning

confidence: 99%

Malonic Anhydrides, Challenges from a Simple Structure

Perrin

2022

J. Org. Chem.

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After many years of unsuccessful attempts, monomeric malonic anhydrides were prepared by ozonolysis of ketene dimers, a procedure validated by model studies. The structure proof relied most heavily on IR absorption at 1820 cm −1 and a Raman band at 1947 cm −1 . Malonic anhydrides are unstable, decomposing below room temperature to a ketene plus carbon dioxide. Surprisingly, according to kinetic studies, the dimethyl derivative is slightly less unstable than the parent, and the monomethyl is the fastest to decompose, with an enthalpy of activation of only 12.6 kcal/mol. Computations rationalize this behavior in terms of a concerted [2 s + 2 a ] cycloreversion that requires a more highly organized transition state, as also manifested by a negative entropy of activation.

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“…In 2014, the group of Billard valued uranium hexafluoride (UF 6 ) as a fluorinating agent. 48 They examined its behavior towards different functions such as alcohols or carbonyl derivatives. To their delight, they could observe the formation of acyl fluorides in moderate to excellent yields starting from the corresponding acid derivatives (Scheme 30).…”

Section: Uranium Hexafluoridementioning

confidence: 99%

Recent Advances in the Synthesis of Acyl Fluorides

Gonay¹,

Batisse²,

Paquin³

2020

Synthesis

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Acyl fluorides are valuable intermediates in organic synthesis. They are increasingly employed in peptide synthesis, in challenging esterification and amidation reactions or in transition-metal-catalyzed transformations. This review summarizes recent advances in their preparation.1 Introduction2 Nucleophilic Fluorination2.1 α-Fluoroamine Reagents2.2 Sulfur-Based Reagents2.3 Metal Catalysts2.4 Phosphorus-Based Reagents2.5 N,N′-Dicyclohexylcarbodiimide/HF·Pyridine2.6 Uranium Hexafluoride2.7 Bromine Trifluoride3 Radical Fluorination4 Conclusion

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(Re)Investigation of the reactivity of uranium hexafluoride toward several organic functions at room temperature

Cited by 12 publications

References 17 publications

Monofluorination of Organic Compounds: 10 Years of Innovation

Monofluorination of Organic Compounds: 10 Years of Innovation

Malonic Anhydrides, Challenges from a Simple Structure

Recent Advances in the Synthesis of Acyl Fluorides

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