Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5279501 | Tetrahedron Letters | 2009 | 4 Pages |
Abstract
The reaction of biphenylene (1) with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of DTBB (10 mol %) in THF at room temperature leads to the formation of the dilithiated species I by reductive opening of the four-membered ring. Further reaction of this intermediate with different electrophiles [Electrophile = H2O, D2O, Me3SiCl, t-BuCHO, Et2CO, n-Pr2CO, (CH2)5CO, Ph2CO and adamantanone] at 0 °C yields the corresponding products 2, after hydrolysis with water. Cyclisation of some representative examples of compounds 2 with H3PO4 gives the corresponding dibenzoxepines 3.
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Authors
Victor J. Lillo, Cecilia Gómez, Miguel Yus,