Oxidative conversion of alpha,alpha-disubstituted acetamides to corresponding one-carbon-shorter ketones using hypervalent iodine (lambda5) reagents in combination with tetraethylammonium bromide.
Alpha,alpha-disubstituted acetamides undergo oxidative dehomologation to give one-carbon-shorter ketones when reacted with a hypervalent iodine (lambda(5)) reagent in combination with tetraethylammonium bromide (TEAB) in various solvents. In further studies, one such combination of a hypervalent iodine (lambda(5)) reagent, o-iodoxybenzoic acid, and TEAB has been established as a new, mild, efficient, and general method for the transformation.
Bellale
Eknath V
EV
Department of Pharmaceutical Sciences & Technology, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai 400 019, India.
Bhalerao
Dinesh S
DS
Akamanchi
Krishnacharya G
KG
D000081:Acetamides / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D007455:Iodine / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013696:Temperature; D019789:Tetraethylammonium / Q000737:chemistry*
D000081:Acetamides; D007462:Iodobenzenes; D007659:Ketones; D012997:Solvents; C476101:o-iodoxybenzoic acid; D019789:Tetraethylammonium; D002244:Carbon; D007455:Iodine; D009584:Nitrogen; D010100:Oxygen