74973-18-5Relevant academic research and scientific papers
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.
Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)
Liu, Huan,Wang, Xuemin,Gu, Yonghong
experimental part, p. 1614 - 1620 (2011/04/22)
Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF3·OEt 2 in AcOH at room temperature afforded the corresponding para-acetoxylated products with high regioselectivity. In addition, this reaction could be expanded to the etherification of anilides. In the presence of 2.0 equiv. of PIFA and 2.0 equiv. of BF3·OEt2, the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields. The Royal Society of Chemistry 2011.
