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Electronic effects in a series of stereoisomeric 2-hydro-2-oxo-1,3,2-dioxaphosphorinanes

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

Conclusions

  1. 1.

    The electronic influence of the dioxaphosphorinane ring in cis-trans-stereoisomeric 2-hydro-4-methyl-, 2-hydro-4-phenyl-, and 2-hydro-5,5-dimethyl-4-isopropyl-2-oxo-1,3,2-dioxaphosphorinanes was studied.

  2. 2.

    For a quantitative estimation of the effect of the dioxaphosphorinane ring, we used the dependence of log Kas on ∑σP (Kas is the association constant). For its construction, Kas of p-fluorophenol with various phosphoryl compounds in CCl4 were measured.

  3. 3.

    The phosphoryl group in trans-isomers exhibits a greater proton acceptor capacity than in cisisomers, which follows from the larger values of Kas, ΔH, and ΔνOH.

  4. 4.

    The autoassociation of 2-hydro-2-oxo-1,3,2-dioxaphosphorinanes in CCl4, CS2, and C6H6 was studied.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    E. I. Matrosov, É. E. Nifant'ev, A. A. Kryuchkov & M. I. Kabachnik

Authors
  1. E. I. Matrosov
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  2. É. E. Nifant'ev
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  3. A. A. Kryuchkov
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  4. M. I. Kabachnik
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 530–534, March, 1976.

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Matrosov, E.I., Nifant'ev, É.E., Kryuchkov, A.A. et al. Electronic effects in a series of stereoisomeric 2-hydro-2-oxo-1,3,2-dioxaphosphorinanes. Russ Chem Bull 25, 512–516 (1976). https://doi.org/10.1007/BF01106643

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  • DOI: https://doi.org/10.1007/BF01106643

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