Nitration of Bis(amido)naphthalenes

Article abstract of DOI:10.1021/jo00222a007

Nitration studies have been conducted on the bis(acetamido), bis(p-toluenesulfonamido), and bis(trifluoroacetamido) derivatives of 2,6-diamino-4,8-dinitro- and 1,5-diaminonaphthalene.The bis(trifluoroacetamides) were nitrated readily to produce tetranitro derivatives, whereas the p-toluenesulfonamides and acetamides gave predominantely dinitro products.The tetrakis(trifluoroacetyl) and tetraacetyl derivatives of 1,3,5,7-tetraaminonaphthalene were nitrated to yield di- and mononitro products, respectively.Solvolysis of some of the amides was successful (most facile with trifluoroacetamido), leading to the first preparations of 2,6-diamino-1,4,5,8-tetranitro-, 1,5-diamino-4,8-dinitro-, and 1,5-dinitro-2,4,6,8-tetraaminonaphthalenes.Peracid oxidation of the new diamines or amides failed to yield polynitronaphthalenes.The effect of structure on the course of nitration, solvolysis, and oxidation of the new nitrated naphthalene derivatives is discussed.