Reactions between 2,5-di-t-butyl-1,4-benzoquinone and certain primary aliphatic amines

The title quinone reacts with n-propyl- and n-butyl-amine in the absence of air to give benzoxazoles and 3-amino-2,5-di-t-butyl-1,4-benzoquinone. In the presence of air, the formation of aminated quinone epoxides is observed to be a major reaction. No products were detected in the dark reaction of the title quinone with t-butylamine, but in the presence of light, aminated quinones containing a rearranged side-chain are obtained.