Nitration of triphenylene discotics: synthesis of mononitro-, dinitro- and trinitro-hexaalkoxy triphenylenes

Abstract

Nitration of hexaalkoxytriphenylene has very recently been reported to produce exclusively the 1-nitro-hexaalkoxytriphenylene. We have found that nitration of such discotics is not restricted to only one ring of triphenylene; all the three rings can be nitrated successively to produce mononitro-, dinitro- and trinitro-hexaalkoxytriphenylenes. These nitro-triphenylenes are valuable precursors to several other triphenylene derivatives. Mononitration of monohydroxypenta- alkoxytriphenylene gives the monohydroxy-mononitro derivative, an extremely important precursor to functionalized triphenylene polymers.