Tetrahedron

Functionalization of non-activated C–H bonds in ketones and imines with HF/SbF 5/CCl 4

S Thibaudeau, A Martin-Mingot, MP Jouannetaud…

Index: Thibaudeau, Sebastien; Martin-Mingot, Agnes; Jouannetaud, Marie-Paule; Jacquesy Tetrahedron, 2002 , vol. 58, # 33 p. 6643 - 6649

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Citation Number: 13

Abstract

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 ...

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