Journal of Organic Chemistry p. 4545 - 4551 (1981)
Update date:2022-08-04
Topics:
Jempty, Thomas C.
Gogins, Kitty A. Z.
Mazur, Yehuda
Miller, Larry L.
Adsorption of FeCl3*6H2O onto silica gel produces a supported reagent FeCl3/SiO2.This reagent is insoluble in CH2Cl2 and is used in that solvent for reaction with phenol ethers.Dimethoxy aromatics are coupled to produce biaryls in high yield.Seven examples including both inter- and intramolecular couplings are reported.The effect of various support materials is explored.An electron-transfer mechanism is proposed.Disiloxy aromatics are oxidized to quinones.Ten examples of substituted 1,4-bis(trimethylsiloxy)- or 1,4-bis(tert-butyldimethylsilyloxy)benzene oxidations are reported.In one example the reaction is catalytic in FeCl3, being driven by oxygen.Benzyloxy aromatics are cleaved to phenols.In this reaction FeCl3 acts on a Lewis acid.The importance of coadsorbing the reagent and the aromatic ether in the absence of solvent is demonstrated.
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