51250-74-9Relevant academic research and scientific papers
Synthetic aspects of the oxidative amidation of phenols
Liang, Huan,Ciufolini, Marco A.
experimental part, p. 5884 - 5892 (2010/09/09)
The oxidative amidation of phenols effects the conversion of appropriately substituted phenols into 4-amidodienones ('para-oxidative amidation') or 2-amidodienones ('ortho-oxidative amidation') by the action of hypervalent iodine reagents. The reagent, (diacetoxyiodo)benzene ('DIB') is especially effective in these transformations. This paper focuses on techniques for the desymmetrization of the dienoes thus obtained, leading to the stereocontrolled creation of N-substituted spiro carbons. The methodology creates new opportunities in alkaloid synthesis, as apparent from a number of examples. DIB=PhI(OAc)2. The reaction may be carried out in the intra- or the intermolecular mode.
Oxidation of oximes to nitrile oxides with hypervalent iodine reagents
Mendelsohn, Brian A.,Lee, Shelley,Kim, Simon,Teyssier, Florian,Aulakh, Virender S.,Ciufolini, Marco A.
supporting information; experimental part, p. 1539 - 1542 (2009/08/07)
Iodobenzene diacetate in MeOH containing a catalytic amount of TFA efficiently oxidizes aldoximes to nitrile oxides. The latter may be trapped in situ with olefins in a bimolecular or an intramolecular mode. The new method enables the execution of tandem oxidative dearomatization of phenols/intramolecular nitrile oxide cycloaddition sequences leading to useful synthetic intermediates.
The synthesis of benzhydroximoyl chloride and nitrile oxides under solvent free conditions
Bigdeli, Mohammad A.,Mahdavinia, Gholam Hossein,Jafari, Saeed
, p. 26 - 28 (2008/02/02)
Benzhydroximoyl chlorides were prepared as nitrile oxide precursors with acidic (HCl) silica gel/Oxone in solvent less media in excellent yields with the selective chlorination of aldoximes vs. aromatic substitution. Nitrile oxides were generated by Huisg
