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The reaction of phosphorus trichloride with unsaturated cyclic ketones

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Phosphorus trichloride adds toα,β-unsaturated cyclic ketones with formation after hydrolysts of cyclicγ-oxophosphonic acids.

  2. 2.

    Cyclicγ-oxophosphonic acids of identical structure are obtained by the addition of diethylphosphorous acid toα,β-unsaturated cyclic ketones and the subsequent hydrolysts of the esters formed.

  3. 3.

    The fact that cyclicγ-oxophosphonic acids are formed fromαβ-unsaturated cyclic ketones disproves Conant's hypothesis concerning the mechanism of the addition of phosphorous trichloride toαβ-unsaturated ketones.

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Kabachnik, M.I., Medved, T.Y. The reaction of phosphorus trichloride with unsaturated cyclic ketones. Russ Chem Bull 1, 517–522 (1952). https://doi.org/10.1007/BF01172007

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  • DOI: https://doi.org/10.1007/BF01172007

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