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Diethyl chlorophosphite: a versatile reagent.

Zhou Jie1, Vebumani Rammoorty, Bilha Fischer

  • 1Department of Chemistry, Gonda-Goldschmied Medical Research Center, Bar-Ilan University, Ramat-Gan 52900, Israel.

The Journal of Organic Chemistry
|February 22, 2002
PubMed
Summary
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Diethyl chlorophosphite (DECP) is a versatile reducing agent. This study expands its utility beyond nitro compounds to various oxygenated functional groups, enabling selective, stepwise transformations.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Reaction Methodology

Background:

  • Diethyl chlorophosphite (DECP) has been established as a reducing agent for converting nitro compounds to amines.
  • The need for versatile reagents in organic synthesis is continuous, driving exploration of known compounds for new applications.

Purpose of the Study:

  • To investigate and report the scope of diethyl chlorophosphite (DECP) reactions with a range of oxygenated functional groups.
  • To describe the chemoselectivity of DECP in these new transformations.
  • To establish conditions for sequential, multiple functional group conversions using DECP.

Main Methods:

  • Reaction screening of DECP with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes.
  • Analysis of reaction products to determine chemoselectivity and efficiency.

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  • Optimization of reaction conditions for stepwise functional group modifications.

    • Main Results:

    • DECP demonstrates reactivity with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes.
    • The reagent exhibits controllable chemoselectivity, allowing for targeted functional group transformations.
    • Conditions were developed for performing multiple, sequential conversions on a single molecule.

    Conclusions:

    • Diethyl chlorophosphite (DECP) is a valuable and versatile reagent for the reduction of diverse oxygenated functional groups.
    • The chemoselectivity and ability for stepwise multiple conversions expand the synthetic utility of DECP in organic chemistry.
    • This work provides a foundation for utilizing DECP in complex molecule synthesis and functional group interconversion.