Oxidation of 1-amino-4,5-bis(dimethylamino)naphthalene as a route to the double “proton sponges” based on dibenzo[a,h]phenazine and 1,1′-azonaphthalene

Add time:09/28/2019    Source:infona.pl

Behavior of 4-amino-1-dimethylamino- and 1-amino-4,5-bis(dimethylamino)naphthalenes sharply differs on their treatment with tosyl chloride and oxidation with the ButOK/O2 system. While the former upon the action of tosyl chloride in protic media is transformed to sulfonamide, the latter unexpectedly forms 4,5,11,12-tetrakis(dimethylamino)Dibenzo[a,h]phenazine (cas 226-47-1) in ∼20% yield as a product of the competitive reaction, which represents the earlier unknown type of double “proton sponges”. In contrast to this, the oxidative dimerization of the indicated amines with ButOK/O2 leads to 5,12-bis(dimethylamino)dibenzo[a,h]phenazine and 4,5,4′,5′-tetrakis(dimethylamino)-1,1′-azonaphthalene, respectively. Possible mechanisms of these reactions were considered, as well as problems of coloring, solvatochromism, and protonation of the compounds obtained.

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