2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopentadienone
Structural formula
Van der Waals space-filling model of 2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopentadienone
2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopentadienone sample
Names
Systematic IUPAC name
2,5-bis(4-bromophenyl)-3,4-diphenylcyclopenta-2,4-dien-1-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C29H18Br2O/c30-23-15-11-21(12-16-23)27-25(19-7-3-1-4-8-19)26(20-9-5-2-6-10-20)28(29(27)32)22-13-17-24(31)18-14-22/h1-18H checkY
    Key: AZUZXBNEGFLECE-UHFFFAOYSA-N checkY
  • InChI=1S/C29H18Br2O/c30-23-15-11-21(12-16-23)27-25(19-7-3-1-4-8-19)26(20-9-5-2-6-10-20)28(29(27)32)22-13-17-24(31)18-14-22/h1-18H
    Key: AZUZXBNEGFLECE-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C2=C(C(=O)C(=C2C3=CC=CC=C3)C4=CC=C(C=C4)Br)C5=CC=C(C=C5)Br
Properties
C29H18Br2O
Molar mass 542.270 g·mol−1
Appearance black solid
Related compounds
Related compounds
 Tetraphenylcyclopentadienone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopentadienone is a variant of tetraphenylcyclopentadienone containing 2 bromine atoms at the para positions of the phenyl rings at the 2- and 5- positions of the central cyclopentadienone ring. Like tetraphenylcyclopentadienone, it is a black solid.

Preparation

2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopentadienone may be prepared by the reaction of bis(4-bromobenzyl) ketone with benzil in the presence of base in a double aldol condensation.[1]

Reactions

1,4-bis(4-bromophenyl)-2,3,5,6-tetraphenylbenzene

2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopentadienone reacts with diphenylacetylene in benzophenone or diphenyl ether as solvent, in a Diels-Alder reaction, to form 1,4-bis(4-bromophenyl)-2,3,5,6-tetraphenylbenzene, a variant of hexaphenylbenzene with 2 bromine atoms on the para positions of opposite phenyl rings.[2]

References

  1. ↑ Coan, Stephen B.; Trucker, Donald E.; Beckerr, Ernest I. (1955). "The Absorption Spectra of Tetracyclones. IV". Journal of the American Chemical Society. 77 (1): 60–66. doi:10.1021/ja01606a018.
  2. ↑ Wolfe, James F.; Arnold, F. E. (1981). "Rigid-rod polymers. 1. Synthesis and thermal properties of para-aromatic polymers with 2,6-benzobisoxazole units in the main chain". Macromolecules. 14 (4): 909–915. Bibcode:1981MaMol..14..909W. doi:10.1021/ma50005a004.
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