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No fear of perfluorinated peroxides: Syntheses and solid state structures of surprisingly inert perfluoroalkyl peroxides

Jan H. Nissen, Tony Stüker, Thomas Drews, Simon Steinhauer, Helmut Beckers, Sebastian Riedel – 2019

We report on the solid‐state structures of bis(nonafluoro‐tert‐butyl) peroxide [(F₃C)₃CO]₂ and bis(undecafluoro‐2‐methyl‐2‐butyl) peroxide [(C₂F₅)(F₃C)₂CO]₂. These peroxides were prepared from the corresponding hypofluorites and fluorinated silver wool. The solid‐state structures obtained after in situ crystallisation show unusual COOC dihedral angles of 180°, as well as elongated O−O bonds because of the bulky perfluorinated alkyl groups. The perfluorinated alkyl peroxides are insensitive to both impact (>40 J) and friction (>360 N), and resistant towards mineral acids (HX; X=F, Cl, Br) and elemental halogens (X₂). Ferrocene is oxidized by [(F₃C)₃CO]₂ to [FeᴵᴵᴵCp₂][OC(CF₃)₃].

Titel
No fear of perfluorinated peroxides: Syntheses and solid state structures of surprisingly inert perfluoroalkyl peroxides
Verfasser
Jan H. Nissen, Tony Stüker, Thomas Drews, Simon Steinhauer, Helmut Beckers, Sebastian Riedel
Schlagwörter
Fluorine • Perfluorinated Alkyl • Peroxides • Structures
Datum
2019
Erschienen in
Angew. Chem. Int. Ed. 2019, 58, 3584-3588 (Angew. Chem. 2019, 131, 3622-3626)
Zitierweise
DOI: 10.1002/anie.201814417 (Int. Ed.); 10.1002/ange.201814417
Sprache
eng