Journal article

Publication year: 2024

Journal: Journal of Fluorine Chemistry

Volume number: 276

ISSN: 0022-1139

eISSN: 1873-3328

Open access status: Hybrid

DOI Link: https://doi.org/10.1016/j.jfluchem.2024.110281

Publisher: Elsevier

Abstract: 
While 1,3-dehydro-5,7-difluoroadamantane 11 reacts with SbF 5 in super acid media (SO 2 ClF) to generate the 1,3-dehydroadamant-5,7-diyl dication 1 , 1,3-dehydro-5-fluoroadamantane 12 fails to react analogously to produce the 1,3-dehydroadamant-5-yl cation 9 ; instead, the 3,5-difluoro-1-adamantylcation 13 is formed. We present a computational study that explains this surprising behavior by the initial addition of Sb 2 F 10 to the propellane bond present in 12 . This is computed to be highly exothermic and leads to a zwitterionic (or ion-pair) species, which in turn reacts autocatalytically with HF to produce the observed fluorinated cation 13 , SbF 3 , and SbF 6 - .

Harvard Citation style: Bremer, M. (2024) Unexpected reaction of antimony pentafluoride with a fluorinated propellane, Journal of Fluorine Chemistry, 276, Article 110281. https://doi.org/10.1016/j.jfluchem.2024.110281

APA Citation style: Bremer, M. (2024). Unexpected reaction of antimony pentafluoride with a fluorinated propellane. Journal of Fluorine Chemistry. 276, Article 110281. https://doi.org/10.1016/j.jfluchem.2024.110281