Chemistry:2,5-Bis(4-bromophenyl)-3,4-diphenylcyclopentadienone
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| Names | |
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| Systematic IUPAC name
2,5-bis(4-bromophenyl)-3,4-diphenylcyclopenta-2,4-dien-1-one | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C29H18Br2O | |
| Molar mass | 542.270 g·mol−1 |
| Appearance | black solid |
| Related compounds | |
Related compounds
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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
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
- ↑ 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.
- ↑ 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. doi:10.1021/ma50005a004. Bibcode: 1981MaMol..14..909W.
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