Phosphirene

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Phosphirene
Names
Preferred IUPAC name
1H-Phosphirene
Systematic IUPAC name
Phosphacyclopropene
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/C2H3P/c1-2-3-1/h1-3H
    Key: BHJIMPINIQQPJX-UHFFFAOYSA-N
  • C1=CP1
Properties
C2H3P
Molar mass 58.020 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phosphirene is the hypothetical

organophosphorus compound with the formula C2H2PH. As the simplest cyclic, unsaturated organophosphorus compound, phosphirene is the prototype of a family of related compounds that have attracted attention from researchers.[1]

Phosphirenes, that is substituted phosphirene compounds where one or more of the H's are replaced by organic substituents, are far more commonly discussed than the parent phosphirene. The first example of a phosphirene, 1,2,3-triphenylphosphirene was prepared via trapping of the phosphinidine complex Mo(CO)5PPh with diphenylacetylene.[2]

Placement of the double bond between the carbon atoms provides a 1Hphosphirene in which the phosphorus center is bonded to two carbon atoms and a hydrogen atom. Alternatively, placement of the double bond between the phosphorus center and a carbon atom generates a 2H-phosphirene. The first 2H-phosphirene was synthesized as early as 1987 by Regitz group. However, the chemistry of 2H-phosphirenes was relatively dormant until a series of reports by Stephan group.[3][4]

References

  1. ISBN 978-0-08-096518-5
    .
  2. doi:10.1021/ja00380a029
    .
  3. S2CID 53564701
    .
  4. S2CID 207187997
    .
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