New 1,1-amino hydroperoxides from regioselective oxygenation of 4-(n-arylmethyleneamino)-2,6-di-t-butylphenols.

Abstract

The oxygenation of 4-(N-arylmethyleneamino)-2,6-di-t-butylphenols with Co(Salpr), a five coordinate Co(II0 Schiff base complex, in CH 2Cl 2 results in the regioselective hydroperoxylation at the imino carbon to give N-(l-aryl-l-hydroperoxymethyl)-3,5-di-t-butyl-p-benzoquinone monoimines, which give exclusively the corresponding amides and 2,6-di-t-butyl-p-benzoquinone in an aerobic solution of KOH in 90% EtOH.