N-((n-nitrosoarylamino)methyl)succinimide as a new agent generating aromatic diazotate

TLDR: In this paper, a series of N-[(N-nitrosoarylamino) methyl] succinimides were synthesized, disclosing their syn and anti equilibria in a state of solution.

Abstract: We have newly synthesized a series of N-[(N-nitrosoarylamino) methyl] succinimides, disclosing their syn and anti equilibria in a state of solution. It has been found that these nitrosoamines are capable of furnishing aromatic diazotates in basic media. By allowing the generating aromatic diazotates to react in situ, azo-couplings and triazene formations have been provided. The nitrosoamines behaved in acidic media to suffer a migration of the nitroso group similarly to the Fischer-Hepp migration.