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Diphenylketene

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Diphenylketene
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2,2-Di(phenyl)ethenone
Other names
Diphenylethenone
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C14H10O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H checkY
    Key: ZWJPCOALBPMBIC-UHFFFAOYSA-N checkY
  • InChI=1/C14H10O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H
    Key: ZWJPCOALBPMBIC-UHFFFAOYAQ
  • C1=CC=C(C=C1)C(=C=O)C2=CC=CC=C2
  • O=C=C(c1ccccc1)c2ccccc2
Properties
C14H10O
Molar mass 194.233 g·mol−1
Appearance Red-orange oil
Melting point 8 to 9 °C (46 to 48 °F; 281 to 282 K)
Boiling point 118 to 120 at 1mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Diphenylketene is a chemical substance of the ketene family. Diphenylketene, like most disubstituted ketenes, is a red-orange oil at room temperature and pressure.

Reactivity

Diphenylketene can undergo attack from a host of nucleophiles, including alcohols, amines, and enolates with fairly slow rates. These rates can be increased in the presence of catalysts. At present the mechanism of attack is unknown, but work is underway to determine the exact mechanism.

Synthesis

Diphenylketene is produced by the elimination of hydrogen chloride from diphenylacetyl chloride in the presence of triethylamine.[1]

Preparation of Diphenylketene

References

  1. ^ "DIPHENYLKETENE [Ethenone, diphenyl-]". Organic Syntheses. 52: 36. 1972. doi:10.15227/orgsyn.052.0036. {{cite journal}}: Unknown parameter |authors= ignored (help)