72054-81-0Relevant articles and documents
Organocopper Chemistry of Quinone Bisketals. Application to the Synthaais of Isoprenoid Quinone Systems
Chenard, Bertrand L.,Manning, Michael J.,Raynolds, Peter W.,Swenton, John S.
, p. 378 - 384 (2007/10/02)
The reactions of organocuprates of 1,4-benzoquinone and 1,4-naphthoquinone bisketals are reported.These reagents, formed from the corresponding lithium reagent, cuprous iodide, and dimethyl sulfide react efficiently with allylic bromides (allyl, prenyl, geranyl, and phytyl), often with utilization of greater than one R group of the R2CuLi.Their reactions with acid chlorides and benzyl bromide proceed with acceptable efficiency, but they are unreactive toward a number of other substrates.The utility of this chemistry in the synthesis of menaquinone-2, phylloquinone,cymopol, and cymopol methyl ether is described.
Anodic Oxidation of 1,4-Dimethoxy Aromatic Compounds. A Facile Route to Functionalized Quinone Bisketals.
Henton, Daniel R.,McCreery, Richard L.,Swenton, John S.
, p. 369 - 378 (2007/10/02)
The anodic oxidation of 12 functionalized 1,4-dimethoxybenzene derivatives and 8 functionalized 1,4-dimethoxynaphthalenes has been studied under a variety of conditions.Many substituted 1,4-dimethoxy aromatics afford high yields of the respective quinone bisketals by single-cell anodic oxidation without accurate control of the electrode potential.Oxidizable groups offen complicate the anodic oxidation; however, in some cases protected derivatives of these functionalities can be converted to the bisketals in good yields.Aromatics containing reducible functions can besmoothly oxidized to quinone bisketals by the use of a divided cell.The current efficiencies and the effect of electrode material on selected systems are reported and discussed.
