177995-52-7Relevant articles and documents
Functionalization of non-activated C-H bonds in ketones and imines with HF/SbF5/CCl4
Thibaudeau, Sébastien,Martin-Mingot, Agnès,Jouannetaud, Marie-Paule,Jacquesy
, p. 6643 - 6649 (2007/10/03)
Reaction of cyclic ketones 2-6 and imines 15-17 in HF/SbF5 in presence of CCl4 yield hydroxy or fluoroderivatives, hydride abstraction occurring at a site located far from the functional group. Whereas ketones 2-5 yield only hydroxy derivatives, through cyclic carboxonium ion, imines 15, 16 N-protonated in the media conditions give only fluoroderivatives 18, 19, respectively, after quenching with HF-pyridine. Ring contraction is operative when starting from large membered ring ketones 24 and 25, and imine 26, leading to a mixture of hydroxy or fluoro cyclohexanones and/or cycloheptanones.