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Stereospecificity of alkylation of phosphite anion in electrochemical version of the Michaelis-Becker reaction

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Benzylation ofcis2-hydro-2-oxo-4-methyl-1,3,2-dioxaphosphorinane in the electro-chemical version of the Michaelis-Becker reaction occurs stereospecifically with retention of the stereochemistry of the hydrophosphoryl center and affords stereochemically pure 2-benzyl-2-oxo-4-methyl-1,3,2-dioxaphosphorinane (yield 60–70 %). The structure of this compound was determined by X-ray diffraction analysis. The mechanism of the process was discussed.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    V. A. Petrosyan, E. E. Nifant, M. E. Nryazymbetov, R. K. Magdeeva, N. S. Magomedova & V. K. Bel My

Authors
  1. V. A. Petrosyan
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  2. E. E. Nifant
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  3. M. E. Nryazymbetov
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  4. R. K. Magdeeva
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  5. N. S. Magomedova
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  6. V. K. Bel My
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriva Khimicheskaya, No. 2, pp. 444–446, February, 1996.

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Petrosyan, V.A., Nifant, E.E., Nryazymbetov, M.E. et al. Stereospecificity of alkylation of phosphite anion in electrochemical version of the Michaelis-Becker reaction. Russ Chem Bull 45, 427–429 (1996). https://doi.org/10.1007/BF01433988

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  • DOI: https://doi.org/10.1007/BF01433988

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