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词条 1,3-dipole
释义

  1. References





From top to bottom,
azides, nitrones, and
nitro compounds are
examples of 1,3-dipoles.

In organic chemistry, a 1,3-dipolar compound or 1,3-dipole is a dipolar compound with delocalized electrons and a separation of charge over three atoms. They are reactants in 1,3-dipolar cycloadditions.[1][2]

Known 1,3-dipoles are:

  • Azides (RN3)
  • Ozone (O3)
  • Nitro compounds (RNO2)
  • Diazo compounds (R2CN2)
  • Some oxides
    • Azoxide compounds (RN(O)NR)
    • Carbonyl oxides (Criegee zwitterions)[3][4]
    • Nitrile oxides (RCN-O)
    • Nitrous oxide (N2O)
    • Nitrones (R2CN(R)O)
  • Some imines:
    • Azomethine imine
    • Nitrilimines (RCN-NR, analogous to nitrile oxide)
    • Carbonyl imines
  • Some ylides
    • Azomethine ylide
    • Nitrile ylide (RCNCR'2)
    • Carbonyl ylide
    • Thiosulfines (R2CSS)

References

1. ^{{cite book|title=Advanced Organic Chemistry|chapter=Part A: Structure and mechanisms|author=Francis A. Carey, Richard J. Sundberg |edition=5, illustrated |publisher=Springer |year=2007 |page=874 |isbn=978-0-387-44897-8}}
2. ^IUPAC Gold Book dipolar compounds
3. ^https://www.organic-chemistry.org/namedreactions/ozonolysis-criegee-mechanism.shtm Ozonolysis mechanism on Organic Chemistry Portal site
4. ^Li, Jie Jack: Criegee mechanism of ozonolysis Book: Name Reactions. 2006, 173-174, {{DOI|10.1007/3-540-30031-7_77}}

1 : Organic chemistry

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