A new antiaromatic compound: 1,4-biphenylenequinone synthesis and trapping reactions: can a quinone unit stabilize the cyclobutadiene?

2001-12-03
Kilic, H
Balcı, Metin
The photooxygenation of 4a,8b-dihydrobiphenylene affords an endoperoxide. NEt3-catalyzed rearrangement of this endoperoxide gave the corresponding hydroxy enone, while the CoTPP-catalyzed rearrangement afforded a bisepoxide. MnO2 oxidation of hydroxy enol leads to 4a,8b-dihydrobiphenylene-1,4-dione. The NIBS bromination of this dione produces mono- and dibromides. NEt3-supported elimination of monobromide and zinc elimination of dibromide afforded the target compound, 1,4-biphenylenequinone, which was trapped as the dimer and cycloadducts with cyclopentadiene and anthracene, respectively. Furthermore, 1,4-biphenylenequinone was generated upon oxidation of biphenylene-1,4-diol with bis(trifluoroacetoxy)iodobenzene (PIFA). The stability and reactivity of the title compound is discussed. (C) 2001 Elsevier Science Ltd. Ail rights reserved
Citation Formats
H. Kilic and M. Balcı, “A new antiaromatic compound: 1,4-biphenylenequinone synthesis and trapping reactions: can a quinone unit stabilize the cyclobutadiene?,” TETRAHEDRON, vol. 57, no. 49, pp. 9889–9897, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52117.