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| Names | |||
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| Other names 1,2-Oxaphosphetane 1,3-Oxaphosphetane | |||
| Identifiers | |||
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3D model (JSmol) |
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| Properties | |||
| C2H5OP | |||
| Molar mass | 76.035 g·mol−1 | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Anoxaphosphetane is amolecule containing a four-membered ring with onephosphorus, oneoxygen and twocarbon 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 theWittig reaction and related reactions such as theSeyferth–Gilbert homologation and theHorner–Wadsworth–Emmons reaction.[2]Edwin Vedejs'sNMR 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 byX-ray crystallography andNMR. Although relatively stable, thermal decomposition of these oxaphosphetanes gave a phosphonium salt, which slowly dissociated to theWittig reaction starting materials, the carbonyl and olefin compounds.
