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Carbomethoxymethylenetriphenylphosphorane

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Carbomethoxymethylene­triphenylphosphorane
Names
Preferred IUPAC name Methyl (triphenyl-λ-phosphanylidene)acetate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 220-018-4
PubChem CID
UNII
InChI
  • InChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3Key: NTNUDYROPUKXNA-UHFFFAOYSA-N
SMILES
  • COC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark GHS06: Toxic
Signal word Danger
Hazard statements H301, H315, H319, H335
Precautionary statements P261, P264, P270, P271, P280, P302+P352, P304+P340, P305+P351+P338, P321, P330, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Carbomethoxymethylenetriphenylphosphorane is a chemical compound used in organic syntheses. It contains a phosphorus atom bound to three phenyl groups, and doubly bound to the alpha position of methyl acetate. It undergoes a Wittig reaction. It is used in the Vitamin B12 total synthesis.

Production

Carbomethoxymethylenetriphenylphosphorane can be made via a multistep reaction using bromoacetic acid, dicyclohexylcarbodiimide, and triphenylphosphine. This makes a phosphonium salt, which is converted to the final product by sodium carbonate in water.

Reactions

Carbomethoxymethylenetriphenylphosphorane reacts with aldehydes to give a two carbon atom extension. The carbomethoxymethylene group replaces the oxygen of the aldehyde to give a trans- double bond.

References

  1. ^ Keck, Gary E.; Boden, Eugene P.; Mabury, Scott A. (March 1985). "A useful Wittig reagent for the stereoselective synthesis of trans-.alpha.,.beta.-unsaturated thiol esters". The Journal of Organic Chemistry. 50 (5): 709–710. doi:10.1021/jo00205a036.
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