5455-67-4Relevant articles and documents
Copper-catalyzed synthesis of azaspirocyclohexadienones from ∝-azido- N -arylamides under an oxygen atmosphere
Chiba, Shunsuke,Zhang, Line,Lee, Jian-Yuan
supporting information; experimental part, p. 7266 - 7267 (2010/08/05)
A copper-catalyzed reaction of ∝-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from ∝-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C-O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O2 was found to be incorporated into the cyclohexadienone moiety.
Efficient radical oxygenation of α-lodocarboxylic acid derivatives
Kihara, Nobuhiro,Ollivier, Cyril,Renaud, Philippe
, p. 1419 - 1422 (2008/02/09)
(equation presented) Treatment of α-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding α-hydroxy add derivatives This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of riethylborane and oxygen, with the α-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimanation product is observed tertiary iodides are efficiently converted to alcohos, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.