A phosphoryl to spiro-bicyclophosphorane transformation via β-amidic proton elimination in phosphorylated hydrazides
作者: Khodayar GholivandHamid R. MahzouniForoogh MolaeiAli A. Kalateh
作者单位: 1Department of Chemistry, Faculty of Basic Sciences, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran
刊名: Tetrahedron Letters, 2012, Vol.53 (44), pp.5944-5947
来源数据库: Elsevier Journal
DOI: 10.1016/j.tetlet.2012.08.105
关键词: 2 J PH Coupling constantHydrazidePhosphorylSpiro-bicyclophosphorane
英文摘要: Abstract(#br)The reaction between phosphoryl-containing reagents and hydrazides has been studied. The tetrahedral phosphoryl structure is transformed into a spiro-bicyclophosphorane system with trigonal bipyramidal geometry by the elimination of a β-amidic proton in the reaction between a hydrazide and phosphoryl reagents with at least two leaving groups (Cl) bound to the phosphorus atom, such as POCl 3 or PhPOCl 2 . In the spiro-bicyclophosphorane structure, the CN imine bond is formed upon β-amidic proton elimination, leading to the conversion of the CO into a C–O bond and the formation of a P–O bond. All of these structural rearrangements are supported by X-ray crystallography data, and NMR and IR experiments.
全文获取路径: Elsevier  (合作)
影响因子:2.397 (2012)