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Oxaphosphetane

Chemical compound From Wikipedia, the free encyclopedia

Oxaphosphetane
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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.

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Stick model of a 1,2-oxaphosphetane that has been isolated and characterised by X-ray crystallography.[1]

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.

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