81027-90-9Relevant academic research and scientific papers
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.
Fluorination or hydroxylation of non activated C-H bonds in amides and ketones using CCl4 or NBS in superacids
Martin, Agnes,Jouannetaud, Marie-Paule,Jacquesy, Jean-Claude
, p. 2967 - 2970 (2007/10/03)
Amides and ketones are fluorinated or hydroxylated in HF-SbF5 in the presence of CCl4 or NBS, reaction occurring at a carbon far located from the functional group.
Decarbonylation of Tetrahydrofuran-2-carboxylic Acids and Tetrahydropyrane-2-carboxylic Acids in Concentrated Sulfuric acid: Formation of Oxonium Ions
Bates, Hans Aaron
, p. 2490 - 2493 (2007/10/02)
Tetrahydrofuran-2-carboxylic acids 1, 3, and 5 readily decarbonylate in 96percent sulfuric acid, generating stable oxonium ions 2, 4, and 6, respectively.Analogously, tetrahydropyran-2-carboxylic acids 7, 9, 12, and 14a produce oxonium ions 8, 10, 13, and 15, respectively.These oxonium ions are quite stable, with the exception of 10, which partially isomerizes to 11, and 13, which rearranges to ions 17 and 21.Details in the transformation of oxonium ion 15 into lactone 23 by way of open chain acid 22a were elucidated.
