693285-59-5Relevant articles and documents
A mild oxidation of deactivated naphthalenes and anthracenes to corresponding para-quinones by N-bromosuccinimide
Natarajan, Palani,Vagicherla, Vinuta Devi,Vijayan, Muthana Thevar
, p. 3511 - 3515 (2014)
A new method to synthesize 1,4-naphthoquinone and 9,10-anthraquinone from naphthalene and anthracene functionalized with either -CHO or -COOH groups, using N-bromosuccinimide (NBS) in aqueous N,N-dimethylformamide at 75-80 °C, has been developed. Further, -CN and -CONH2 functionalized naphthalenes and anthracenes can also be transformed into respective para-quinones in a one pot reaction, after successive acid hydrolysis and subsequent reaction with NBS. We believe that the present finding may serve as a valuable alternative to the classical approaches for the synthesis of polycyclic quinones from polyaromatic carbaldehydes through Dakin oxidation followed by further oxidation of the resulting hydroquinone by heavy metal oxides.