Phosphetane

Phosphetane
Names
	Preferred IUPAC name Phosphetane
Identifiers
CAS Number	287-26-3;
3D model (JSmol)	Interactive image;
ChemSpider	24770404;
PubChem CID	23356115;
CompTox Dashboard (EPA)	DTXSID90633326 ;
	InChI InChI=1S/C3H7P/c1-2-4-3-1/h4H,1-3H2 Key: RVZJVYCTFGOEHX-UHFFFAOYSA-N;
	SMILES C1CPC1;
Properties
Chemical formula	C3H7P
Molar mass	74.063 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

Phosphetane is a four membered phosphorus heterocycle.[1]

Synthesis

Phospentane can be generated via a Wurtz-type coupling of an appropriately halogenated dialkylphosphine

$\mathrm {BrCH_{2}PHCH_{2}CH_{2}Br+Mg{\xrightarrow {THF}}MgBr_{2}+}$

Reactions and applications

Phosphetane and its derivatives are largely limited to academic interest. Exhaustive P-alkylation gives the corresponding phosphonium-salt (phosphetanium), these were used in the early examples of the Allen–Millar–Trippett rearrangement.[2]

References

Marinetti, Angela; Carmichael, Duncan (January 2002). "Synthesis and Properties of Phosphetanes". Chemical Reviews. 102 (1): 201–230. doi:10.1021/cr990135r.
Fishwick, S. E.; Flint, J.; Hawes, W.; Trippett, S. (1967). "Ring expansion in the alkaline hydrolysis of phosphetanium salts". Chemical Communications (London) (21): 1113. doi:10.1039/C19670001113.

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[Rev-1] Marinetti, Angela; Carmichael, Duncan (January 2002). "Synthesis and Properties of Phosphetanes". Chemical Reviews. 102 (1): 201–230. doi:10.1021/cr990135r.

[2] Fishwick, S. E.; Flint, J.; Hawes, W.; Trippett, S. (1967). "Ring expansion in the alkaline hydrolysis of phosphetanium salts". Chemical Communications (London) (21): 1113. doi:10.1039/C19670001113.