Syntheses and utilizations of pyrroline-nitroxide- and tetrahydropyridine-nitroxide-based α-ketophosphonates, β-ketophosphonates, and a bisphosphonate

Syntheses and Study of a Pyrroline Nitroxide Condensed Phospholene Oxide and a Pyrroline Nitroxide Attached Diphenylphosphine

“…These various applications require numerous paramagnetic scaffolds adjusted to different utilizations. Our idea is to combine various phosphorus-containing functional groups with nitroxides, which may offer fascinating possibilities for synthetic, structural and biological studies and the utilization of these new compounds [ 6 , 7 ]. In continuation of our interest in the synthesis of nitroxide-based phosphorus compounds, we have promoted the synthesis of phosphorus-containing heterocycles condensed with pyrroline nitroxide and pyrroline nitroxide-diphenylphosphine and pyrroline nitroxide-diphenylphosphine oxide compounds.…”

Synthesis of 3,4-Disubstituted Pyrroline Nitroxides Containing Diphenylphosphane or Diphenylphosphane Oxide Substituents

“…The mixture was extracted with EtOAc (2 × 15 mL) and the combined extracts were dried (MgSO 4 ), oxidized with PbO 2 (478 mg, 2.00 mmol) to convert hydroxylamine into nitroxide, filtered, and evaporated. The residue was purified by flash chromatography ( (12), 352 (15), 337 (100), 201 (30), 183 (27), 107 (22), 91 (17).…”

“…Organophosphorus compounds are a crucial molecular class in synthetic chemistry because of their applicability as building blocks in ligands of catalysts. In recent years, our laboratory successfully investigated reactions on stable free nitroxide radicals (Arbuzov, 12 Kabachnik-Fields, 13 McCormac, 14 and phospha-Brook rearrangement 15 ), which yield-ed new paramagnetic organophosphorus compounds. In continuation of our research on pyrroline nitroxides diversely substituted with diphenylphosphane, 14 diphenylphosphane oxide, 14 or phosphonate ester, 12 we evaluated 3,4-disubstituted phosphorus-containing pyrroline nitroxide free radicals.…”