Abstract
Addition of bis(pentafluorophenyl)phosphinous acid to α,β-alkenones and α,β,β’-alkene-diones in anhydrous Et2O (the solvent, in which the P-OH tautomeric form predominates) proceeds rapidly and regiospecifically at the C=C bond of the substrate at room temperature in the absence of catalysts. The reaction leads to bis(pentafluorophenyl)phosphorylated alkanones and alkanediones, as a rule, in the yields close to quantitative and can be considered as a highly efficient method for the synthesis of the corresponding functionalized phosphine oxides. The structures of obtained compounds were established by IR and NMR spectroscopy and X-ray diffraction analysis.
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Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2317–2324, October, 2014.
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Goryunov, E.I., Goryunova, I.B., Nelyubina, Y.V. et al. Bis(pentafluorophenyl)phosphinous acid in the synthesis of P,P-bis(pentafluorophenyl)phosphorylalkanones and -alkanediones. Russ Chem Bull 63, 2317–2324 (2014). https://doi.org/10.1007/s11172-014-0741-1
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DOI: https://doi.org/10.1007/s11172-014-0741-1