Diphenylketene

Diphenylketene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2,2-Diphenylethen-1-one
Other names
Diphenylethenone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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 stable disubstituted ketenes, is a red-orange oil at room temperature and pressure. Due to the successive double bonds in the ketene structure R1R2C=C=O, diphenyl ketene is a heterocumulene. The most important reaction of diphenyl ketene is the [2+2] cycloaddition at C-C, C-N, C-O, and C-S multiple bonds.[1]

  1. ^ Ulrich, H. (1967), Cycloaddition Reactions of Heterocumulenes, New York: Academic Press, p. 374