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Heteroorganic betaines

Reactions of betaines containing the+P−C−Si−S− fragment

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The [Ph3P+−CMe2−SiMe2−SEt]Br− salt was prepared by the reaction of betaine Ph3P+−CMe2SiMeR−S− (1a: R=Me) with EtBr. Acetylation of betaine1a or Et3P+−CHMeSiMe2−S− (2a) afforded 2,2,6-trimethyl-1,3-dioxa-2-silacyclohex-5-ene-4-thione

or the [Et3P+−CHMeSiMe2Cl]Cl− salt depending on the reagent ratio. The reactions of betaines1a, b (1b: R=Ph) or2 with compounds (R3Sn)2X (X=O or NMe) can be used for the generation of silanones [RMeSi=O] and silaneimines [RMeSi=NMe] in solutions. The reactivity of betaines Ph3P+−CHR1SiMeR2−S− (R1=H or Me and R2=Me or Ph) is determined by the equilibrium between the zwitterionic and ylide Ph3P=CR1SiMeR2SH tautomers that exist in solutions.

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Authors and Affiliations

  1. State Research Institute of the Chemistry and Technology of Organoelement Compounds, State Research Center of the Russian Federation, 38 sh. Entuziastov, 111123, Moscow, Russian Federation

    I. V. Borisova, N. N. Zemlyanskii, A. K. Shestakova & E. A. Chernyshev

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

    Yu. A. Ustynyuk

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    V. N. Khrustalev

Authors
  1. I. V. Borisova
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  2. N. N. Zemlyanskii
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  3. A. K. Shestakova
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  4. V. N. Khrustalev
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  5. Yu. A. Ustynyuk
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  6. E. A. Chernyshev
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Additional information

For Part 1, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 935–942, May, 2000.

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Borisova, I.V., Zemlyanskii, N.N., Shestakova, A.K. et al. Heteroorganic betaines. Russ Chem Bull 49, 933–941 (2000). https://doi.org/10.1007/BF02494721

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  • DOI: https://doi.org/10.1007/BF02494721

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