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New heteroorganic betaines containing the (+)E15—C—E14—X(–) and (+)E15—C—E14(–) structural fragments (E15 = P, As; E14 = Si, Ge, Sn; X = C, S, O, NR)

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Abstract

The review surveys the data on the reactions of phosphorus and arsenic ylides with compounds containing E=X bonds (E = C, Si, Ge, or Sn; X = C or S), cyclic oligomers (R2ES)n (n = 2 or 3), and heavier analogs of carbenes. These reactions give rise to two new classes of heteroorganic betaines containing the (+)E15—C—E14—X(–) (I) and (+)E15—C—E14(–) (II) (E15 = P or As; E14 = Si, Ge, or Sn; X = C or S) structural fragments. Procedures for the synthesis of these compounds, their reactivities, the X-ray diffraction structures, and the electronic structures established by high-level quantum-chemical calculations are considered in detail. The carbon analogs of betaines of type I, viz., compounds bearing the (+)P—C—C—X(–) fragment (III), are also discussed. The latter were long considered as possible intermediates in the reactions of compounds containing the polar C=X bond (X = C, O, S, NR, etc.) with phosphorus ylides (classical Wittig and Corey—Chaykovsky reactions and related processes).

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  1. Russian Academy of Sciences, A. V. Topchiev Institute of Petrochemical Synthesis, 29 Leninsky prosp., 119991, Moscow, Russian Federation

    I. V. Borisova & N. N. Zemlyanskii

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation

    M. S. Nechaev & Yu. A. Ustynyuk

  3. Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelement Compounds, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    V. N. Khrustalev

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Borisova, I.V., Nechaev, M.S., Khrustalev, V.N. et al. New heteroorganic betaines containing the (+)E15—C—E14—X(–) and (+)E15—C—E14(–) structural fragments (E15 = P, As; E14 = Si, Ge, Sn; X = C, S, O, NR). Russian Chemical Bulletin 51, 721–753 (2002). https://doi.org/10.1023/A:1016058512075

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