Efficient Synthesis of Alkoxyanthraquinones from Fluoroanthraquinones and Their Preliminary Electrochemistry

Article abstract of DOI:10.1021/jo00060a010

The reaction of 1,8-dichloroanthraquinone with CsF in DMSO under anhydrous conditions affords improved yields of the corresponding difluoro derivative 2.Nucleophilic displacement reactions using simple alkoxide nucleophiles or crown ether derivatives on 2 allows the preparation of 1,8-dialkoxyanthraquinones 5-10 in good to excellent yields.Compounds 8 and 10 exhibit enhanced sodium binding properties upon reduction to the corresponding mono- and dianions.Cation binding enhancements are larger than those previously observed for structurally related systems.