Oxaphosphetane

Oxaphosphetane
1,2-Oxaphosphetane	1,3-Oxaphosphetane
Ball-and-stick model of 1,2-oxaphosphetane	Ball-and-stick model of 1,3-oxaphosphetane
Names
	Other names 1,2-Oxaphosphetane; 1,3-Oxaphosphetane
Identifiers
CAS Number	1,2: 287-36-5 ; 1,3: 25885-35-2 ;
3D model (JSmol)	1,2: Interactive image; 1,3: Interactive image;
ChemSpider	1,2: 14123776;
PubChem CID	1,2: 23373974; 1,3: 20362213;
CompTox Dashboard (EPA)	1,2: DTXSID90633467;
	InChI 1,2: InChI=1S/C2H5OP/c1-2-4-3-1/h4H,1-2H2 Key: JONKIUBSNSUGGZ-UHFFFAOYSA-N; 1,3: InChI=1S/C2H5OP/c1-3-2-4-1/h4H,1-2H2 Key: XIEBRVIWJYCCCK-UHFFFAOYSA-N;
	SMILES 1,2: C1CPO1; 1,3: C1OCP1;
Properties
Chemical formula	C2H5OP
Molar mass	76.035 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

An oxaphosphetane is a molecule containing a four-membered ring with one phosphorus, one oxygen and two carbon atoms. In a 1,2-oxaphosphetane phosphorus is bonded directly to oxygen, whereas a 1,3-oxaphosphetane has the phosphorus and oxygen atoms at opposite corners.

1,2-Oxaphosphetanes are rarely isolated but are important intermediates in the Wittig reaction and related reactions such as the Seyferth–Gilbert homologation and the Horner–Wadsworth–Emmons reaction.^[2] Edwin Vedejs's NMR studies first revealed the importance of oxaphosphetanes in the mechanism of the Wittig reaction in the 1970s.^[3]^[4]

In 2005 the first isolation of 1,2-Oxaphosphetanes (typical Wittig intermediates) was reported.^[5] One of the compounds was characterized by X-ray crystallography and NMR. Although relatively stable, thermal decomposition of these oxaphosphetanes gave a phosphonium salt, which slowly dissociated to the Wittig reaction starting materials, the carbonyl and olefin compounds.

References

^ M. Hamaguchi; Y. Iyamaa; E. Mochizukia; T. Oshima (2005). "First isolation and characterization of 1,2-oxaphosphetanes with three phenyl groups at the phosphorus atom in typical Wittig reaction using cyclopropylidenetriphenylphosphorane". Tetrahedron Letters. 46 (51): 8949–8952. doi:10.1016/j.tetlet.2005.10.086.
^ Byrne, Peter A.; Gilheany, Declan G. (2013). "The modern interpretation of the Wittig reaction mechanism". Chemical Society Reviews. 42 (16): 6670–6696. doi:10.1039/C3CS60105F. hdl:10197/4939. PMID 23673458.
^ Vedejs E (30 July 2004). "Studies in Heteroelement-Based Synthesis". The Journal of Organic Chemistry. 69 (16): 5159–5167. doi:10.1021/jo049360l. PMID 15287757.
^ "Memorial Resolution of the Faculty of the University of Wisconsin-Madison" (PDF). University of Wisconsin-Madison. Archived from the original (PDF) on 9 May 2020. Retrieved 9 May 2020.
^ M. Hamaguchi; Y. Iyamaa; E. Mochizukia; T. Oshima (2005). "First isolation and characterization of 1,2-oxaphosphetanes with three phenyl groups at the phosphorus atom in typical Wittig reaction using cyclopropylidenetriphenylphosphorane". Tetrahedron Letters. 46 (51): 8949–8952. doi:10.1016/j.tetlet.2005.10.086.

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[1] M. Hamaguchi; Y. Iyamaa; E. Mochizukia; T. Oshima (2005). "First isolation and characterization of 1,2-oxaphosphetanes with three phenyl groups at the phosphorus atom in typical Wittig reaction using cyclopropylidenetriphenylphosphorane". Tetrahedron Letters. 46 (51): 8949–8952. doi:10.1016/j.tetlet.2005.10.086.

[2] Byrne, Peter A.; Gilheany, Declan G. (2013). "The modern interpretation of the Wittig reaction mechanism". Chemical Society Reviews. 42 (16): 6670–6696. doi:10.1039/C3CS60105F. hdl:10197/4939. PMID 23673458.

[3] Vedejs E (30 July 2004). "Studies in Heteroelement-Based Synthesis". The Journal of Organic Chemistry. 69 (16): 5159–5167. doi:10.1021/jo049360l. PMID 15287757.

[4] "Memorial Resolution of the Faculty of the University of Wisconsin-Madison" (PDF). University of Wisconsin-Madison. Archived from the original (PDF) on 9 May 2020. Retrieved 9 May 2020.

[5] M. Hamaguchi; Y. Iyamaa; E. Mochizukia; T. Oshima (2005). "First isolation and characterization of 1,2-oxaphosphetanes with three phenyl groups at the phosphorus atom in typical Wittig reaction using cyclopropylidenetriphenylphosphorane". Tetrahedron Letters. 46 (51): 8949–8952. doi:10.1016/j.tetlet.2005.10.086.

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