Synthesis p. 626 - 631 (1985)
Update date:2022-08-03
Topics:
Dietl, F.
Gierer, G.
Merz, A.
The preparation of the 1,4-quinones of benzo<15>crown-5 (1), benzo<18>crown-6 (2), and dibenzo<18>crown-6 (3) and their quinols is described.The quinones are obtained by Fremy salt oxidation of the corresponding 3-hydroxybenzo-crown ethers which are readily accessible by a double protective group synthesis from 1,2,3-trihydroxybenzene.The synthetic pathway also provides a general high yield preparation of 2,3-dialkoxy-1,4-benzoquinones.The new crown ethers are characterised by 1H- and 13C-N.M.R. as well as U.V. spectroscopy.Non-aqueous redox potentials aredetermined by cyclic voltammetry.Crystalline complexes of 1 and 2 with various ammonium, alkali, and alkaline earth cations are also described.
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Doi:10.1021/jacs.0c11968
(2021)Doi:10.1139/V08-037
(2008)Doi:10.1055/s-2008-1042903
(2008)Doi:10.1039/b802204f
(2008)Doi:10.1002/ejoc.200701015
(2008)Doi:10.1016/S0040-4020(01)90767-7
(1971)
