10.1246/cl.1979.1077
The study explores a one-pot synthesis method for N-(t-alkylthio)-p-benzoquinoneimines using t-alkyl thionitrates and p-aminophenols. The researchers found that reacting various p-aminophenols with t-alkyl thionitrates in the presence of anhydrous copper(II) chloride and acetonitrile readily produced the desired N-(t-alkylthio)-p-benzoquinoneimines. The t-alkyl thionitrates, which were prepared by reacting thiols with excess dinitrogen tetraoxide, acted as the key reagents to introduce the t-alkylthio group into the p-benzoquinoneimine structure. The resulting compounds were stable, vivid yellow crystals with strong absorption bands near 400 nm. The study also examined the oxidation of N-(t-butylthio)-p-benzoquinoneimine with m-chloroperbenzoic acid to produce an unstable sulfinyl derivative. The new synthetic method is highlighted for its simplicity and usefulness, especially for synthesizing N-t-alkylthio derivatives of p-benzoquinoneimines.