Synthesis of Novel 1,3,5-Tris(arylazo)benzenes via Pd-Catalyzed Couplings and Cu(I)-Mediated Direct Oxidations
- 28 February 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (7), 2603-2606
- https://doi.org/10.1021/jo035720d
Abstract
A series of novel 1,3,5-tris-azobenzenes were prepared from 1,3,5-trihalobenzene via Pd-catalyzed couplings of N-Boc aryl hydrazines and subsequent Cu(I)-mediated direct oxidations. The oxidation of tris-arylhydrazide provided the azobenzene as a mixture of all four of the possible E/Z-isomers; [E,E,E]-, [E,E,Z]-, [E,Z,Z]-, and [Z,Z,Z]-1,3,5-tris-azobenzenes. A slow removal of the solvent in the dark transformed the isomers into the all-trans, [E,E,E]-isomer.Keywords
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