|
|Section2= |Section3= }} Phosphorine (IUPAC name: phosphinine) is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. Phosphorine is a planar aromatic compound with 88% of the aromaticity of that of benzene. The P-C bond length is 173 pm and the C-C bond lengths center around 140 pm and show little variation. Phosphorine is generally stable against air and moisture and can be handled without special inert atmosphere equipment, so it is different from silabenzene, which is usually not only air- and moisture-sensitive but also thermally unstable without extensive steric protection. This stability of phosphorine comes from the close electronegativities of phosphorus (2.1) and carbon (2.5). The physical and chemical properties of metal complexes bearing phosphorine as a ligand as well as phosphorine itself have been studied extensively. ==History== The first phosphorine is 2,4,6-triphenylphoshorine, which was synthesized by Gottfried Märkl in 1966 from the corresponding pyrylium salt and phosphorus sources, such as phosphine, P(CH2OH)3, and P(SiMe3)3.〔''G. Märkl'', 2,4,6-Triphenylphosphabenzol in (Angewandte Chemie 78, 907–908 (1966) )〕 Unsubstituted phosphorine, which was reported by Arthur J. Ashe III in 1971, is a distillable liquid that is somewhat air-sensitive but stable against hydrolysis. In 1990s, François Mathey developed a methodology for the synthesis of functionalized phosphorines using transition metal mediated reactions including palladium- or nickel-catalyzed coupling reactions. More recently, Mathey and Grundy developed a new ring-opening approach, synthesising a six-membered ring phosphabenzene in a one-pot method from a five-membered phosphole ring. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「phosphorine」の詳細全文を読む スポンサード リンク
|