Investigation of the reaction of hexafluoro-1,4-naphthoquinone with substituted phenols

Abstract

Reaction of hexafluoro-1,4-naphthoquinone with various phenols was studied for the first time. It was shown that sodium acetate is a convenient reagent for implementation of the process. The investigated condensation led exclusively to substitution of two fluorine atoms in the quinone core. Based on performed research the method for preparation of substituted 2,3-diaryloxy-5,6,7,8-tetrafluoronaphthalene-1,4-diones was elaborated. Using similar conditions pentafluorobenzo[a]phenoxazine derivatives were obtained from 2-aminophenols. In contrast to phenols cyclic 1,3-diketones in the reaction with perfluoronaphthoquinone act as C-nucleophiles resulting in fluorinated polycondensed furans. Structures of key obtained products were proved using X-ray analysis.