Reversible nature of the opening of the tetrahydrofuran ring of diphenyl(2-tetrahydrofurylmethyl)phosphine oxide by the diphenylphosphinite anion

  • A. É. Antoshin
  • A. V. Kharitonov
  • E. N. Tsvetkov
Organic Chemistry
  • 19 Downloads

Abstract

The reaction of diphenyl(2-tetrahydrofurylmethyl)phosphine oxide with diphenylphosphonous acid in DMSO in the presence of KOH proceeds with opening of the tetrahydrofuran ring and leads to 4,5- bis(diphenylphosphinyl)pentanol. This product is converted to the starting oxide upon the reaction with diphenylvinylphosphine oxide. 4,5-Bis(diphenylphosphinyl)pentanol is converted to the corresponding tosylate. The action of alcoholates on this tosylate gives 1-ethoxy-4, 5-bis(diphenylphosphinyl)pentane and 1-butoxy-1,5-bis(diphenylphosphinyl)pentane.

Keywords

Oxide DMSO Pentane Phosphine Tetrahydrofuran 

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Literature cited

  1. 1.
    A. V. Kharitonov, A. É. Antoshin, and E. N. Tsvetkov, Zh. Obshch. Khim.,57, 2395 (1987).Google Scholar
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    Organic Syntheses [Russian translation], Coll. Vol. 3, Izd. Inos. Lit., Moscow (1952), p. 374.Google Scholar
  3. 3.
    N. A. Bondarenko and E. N. Tsvetkov, USSR Inventor's Certificate No. 1,351,936; Byull. Izobert., No. 42 Mr, (1987).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • A. É. Antoshin
    • 1
  • A. V. Kharitonov
    • 1
  • E. N. Tsvetkov
    • 1
  1. 1.Institute of Physiologically Active CompoundsAcademy of Sciences of the USSRChernogolovka

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