Phosphirene

Phosphirene
Names
	Preferred IUPAC name 1H-Phosphirene
	Systematic IUPAC name Phosphacyclopropene
Identifiers
CAS Number	157-19-7;
3D model (JSmol)	Interactive image;
ChemSpider	24771513;
PubChem CID	15786925;
	InChI InChI=1S/C2H3P/c1-2-3-1/h1-3H Key: BHJIMPINIQQPJX-UHFFFAOYSA-N;
	SMILES C1=CP1;
Properties
Chemical formula	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

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

^ 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.
^ 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.
^ 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.
^ 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. hdl:1983/bc270929-86d1-4526-bc0b-803a533312a3. PMID 29272583. S2CID 207187997.

Quin, L. D. (2000). A Guide to Organophosphorus Chemistry. Wiley-Interscience. ISBN 0-471-31824-8.

[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. hdl:1983/bc270929-86d1-4526-bc0b-803a533312a3. PMID 29272583. S2CID 207187997.

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