Acylarylnitrosamines. Part III. Decomposition of 2,5-di-(N-nitrosoacetamido)-1,4-di-t-butylbenzene and related compounds

Abstract

Decomposition of 2,5-di-(N-nitrosoacetamido)-1,4-di-t-butylbenzene in benzene gives 2,5-di-t-butylhydroquinone diacetates as the major identifiable product. Contrary to predictions based on corresponding reactions of N-nitroso-o-t-butyl- and N-nitroso-2,5-di-t-butyl-acetanilides, no evidence for aryne (or a bis-aryne) was found. Further, there is evidence that the reaction does not proceed via 4-acetoxy-N-nitroso-2,5-di-t-butylacetanilide, decomposition of which gives a different pattern of products including acetic anhydride, in high yield, and 2,5-di-t-butyl-p-benzoquinone. Decomposition of the related p-acetoxy-N-nitrosoacetanilide in the presence of aniline gave acetanilide indicating the presence of an acylating agent, this suggests that in both of these reactions deacylation to give derivatives of benzenediazonium-4-olate may occur.