Synthesis of unsymmetrically substituted phosphane oxides (R(1)R(2)P(O)H) and phosphinous acids (R(1)R(2)POH).

This paper describes the synthesis of unsymmetrically substituted phosphinous acids and phosphane oxides featuring at least one electron-withdrawing pentafluoroethyl group. The presence of a diethylamino function as a protecting group allows a selective reaction of RClPNEt2 (R=CF3 , C6 F5 , C6 H5 ) with LiC2 F5 . On treatment with para-toluenesulfonic acid the isolated aminophosphanes R(C2 F5 )PNEt2 are readily converted into the corresponding phosphinous acids or phosphane oxides, respectively. Investigation of the tautomeric equilibrium between oxide and acid tautomer revealed (CF3 )(C2 F5 )POH as a stable phosphinous acid, whereas the pentafluorophenyl and phenyl derivatives constitute a solvent dependent equilibrium between the acid and the oxide tautomer. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Nadine Allefeld, Michael Grasse, Nikolai Ignat'ev, Berthold Hoge. Synthesis of unsymmetrically substituted phosphane oxides (R(1)R(2)P(O)H) and phosphinous acids (R(1)R(2)POH). Chemistry (Weinheim an der Bergstrasse, Germany). 2014 Jul 7;20(28):8615-20

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PMID: 24842615

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