Phosphirene

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]

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).
Infobox references

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. François Mathey; Manfred Regitz (1996). "Phosphiranes, Phosphirenes, and Heavier Analogues". Comprehensive Heterocyclic Chemistry II. Vol. 1A. pp. 277–304. doi:10.1016/B978-008096518-5.00008-3. ISBN 978-0-08-096518-5.
  2. Angela Marinetti; Francois Mathey; Jean Fischer; Andre Mitschler (1982). "Generation and Trapping of Terminal Phosphinidene Complexes. Synthesis and X-ray Crystal Structure of Stable Phosphirene Complexes". J. Am. Chem. Soc. Vol. 104. pp. 4484–5. doi:10.1021/ja00380a029.
  3. Liu, Liu Leo; Zhou, Jiliang; Cao, Levy L.; Stephan, Douglas W. (2018-11-15). "Facile Cleavage of the P=P Double Bond in Vinyl-Substituted Diphosphenes". Angewandte Chemie International Edition. 58 (1): 273–277. doi:10.1002/anie.201812592. ISSN 1521-3757. PMID 30444313. S2CID 53564701.
  4. Liu, Liu Leo; Zhou, Jiliang; Cao, Levy L.; Andrews, Ryan; Falconer, Rosalyn L.; Russell, Christopher A.; Stephan, Douglas W. (2017-12-22). "A Transient Vinylphosphinidene via a Phosphirene–Phosphinidene Rearrangement" (PDF). Journal of the American Chemical Society. 140 (1): 147–150. doi:10.1021/jacs.7b11791. PMID 29272583. S2CID 207187997.
  • Quin, L. D. (2000). A Guide to Organophosphorus Chemistry. Wiley-Interscience. ISBN 0-471-31824-8.
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