Triphenylcarbethoxymethylenephosphorane

Triphenylcarbethoxymethylenephosphorane is an organophosphorus compound with the chemical formula Ph3PCHCO2Et (Ph = phenyl, Et = ethyl). It is a white solid that is soluble in organic solvents.

Triphenylcarbethoxymethylene­phosphorane
Names
Preferred IUPAC name
Ethyl (triphenyl-λ5-phosphanylidene)acetate
Other names
(2-Ethoxy-2-oxoethylidene)triphenylphosphorane

(Carbethoxymethylene)triphenylphosphorane
(Carbethoxymethylidene)triphenylphosphorane
(Ethoxycarbonylmethylidene)triphenylphosphorane

Ethyl (triphenylphosphoranylidene)acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.865 Edit this at Wikidata
UNII
  • InChI=1/CH2N2O4/c4-2(5)1-3(6)7/h1H2
  • O=C(OCC)C=P(c1ccccc1)(c2ccccc2)c3ccccc3
Properties
C22H21O2P
Molar mass 348.382 g·mol−1
Melting point 124 to 129 °C (255 to 264 °F; 397 to 402 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The compound is a Wittig reagent. It is used to replace oxygen centres in ketones and aldehydes with CHCO2Et.[1]

References

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  1. ^ Lang, R. W.; Hansen, H.-J. (1984). "α-Allenic Esters from α-Phosphoranylidene Esters and Acid Chlorides: Ethyl 2,3-Pentadienoate" (PDF). Organic Syntheses. 62: 202{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 7, p. 232.