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10039-56-2Relevant articles and documents
Phosphaketenes as building blocks for the synthesis of triphospha heterocycles
Heift, Dominikus,Ben?, Zoltán,Grützmacher, Hansj?rg
, p. 11326 - 11330 (2014)
Unsaturated phosphorus compounds, such as phosphaalkenes and phosphaalkynes, show a versatile reactivity in cycloadditions. Although phosphaketenes (R-P=C=O) have been known for three decades, their chemistry has remained limited. Herein, we show that heteroatom-substituted phosphaketenes, R3E-P=C=O (E=Si, Sn), are building blocks for silyl- and stannyl-substituted five-membered heterocycles containing three phosphorous atoms. The structure of the heterocyclic anion depends on the nature of the tetrel atom involved. Although the silyl analogue [P3C 2(OSiR3)2]- is an aromatic 1,2,4-triphospholide, the stannyl compound [P(CO)2(PSnR 3)2]- is a 1,2,4-triphosphacyclopenta-3,5- dionate with a delocalized OCPCO fragment. Because of their anionic character, these compounds can easily be used as building blocks, for example, in the preparation of a silyl-functionalized hexaphosphaferrocene or the parent 1,2,4-triphosphacyclopenta-3,5-dionate [P(CO)2(PH)2] -. NMR spectroscopic investigations and computations have shown that the heterocycle-formation reactions presented herein are remarkably complex. Cycle time! The reaction of Na(OCP) with tetrelhalides, R3EX (E=Si, Sn), gives silyl- and stannyl-substituted five-membered heterocycles containing three phosphorous atoms. Phosphaketenes, R3E-P=C=O, are intermediates, which react with Na(OCP) as a P- transfer reagent to the final products (see scheme; Tf=triflucromethanesulfonyl).
Lindner, L.,Harbottle, G.
, p. 386 - 387 (1960)
Ipatiew, V. N.,Usachev, P. V.
, p. 300 - 302 (1935)