859944-09-5Relevant academic research and scientific papers
Efficient iodine-mediated beckmann rearrangement of ketoximes to amides under mild neutral conditions
Ganguly, Nemai C.,Mondal, Pallab
, p. 3705 - 3709 (2010)
Aryl ketoximes readily underwent Beckmann rearrangement to give N-substituted amides in excellent yields on electrophilic activation by elemental iodine in anhydrous acetonitrile under reflux. The main advantages of this environmentally friendly protocol include a high selectivity as a result of the absence of any accompanying deprotection to form the parent ketones as byproducts, mild neutral conditions, procedural simplicity, and particularly ease of isolation of the products.
Stannous chloride dihydrate-mediated efficient access to secondary and primary amides from oximes
Ganguly, Nemai C.,Nayek, Subhasis,Chandra, Sumanta
, p. 1695 - 1702 (2014/01/17)
Highly selective, efficient and expeditious Beckmann rearrangement of a wide range of ketoximes to secondary amides (20 examples) has been accomplished using stoichiometric amount of stannous chloride dihydrate in the presence of nucleophilic additive, tetra-n-butylammonium iodide (TBAI) (10 moI%) and 4 ? MS in dry acetonitrile at reflux temperature. Aldoximes delivered primary amides through intermediacy of nitriles upon heating with an equimolar amount of SnCl2·2H2O and DBU in dry toluene at reflux in good to acceptable yields (12 examples). Utilization of mild Lewis acid, inexpensive rack reagents and procedural simplicity including easy isolation of products are key advantageous features of the protocol.
