N,N-bis(quinonyl)amines; synthesis and X-ray structure

The preparation of several symmetrical and nonsymmetrical N,N-bis(quinonyl)amines is reported. These compounds, which have two quinones separated by one amino group, were obtained by an unexpected reaction of primary or secondary substituted aminoquinones. While not nucleophilic enough to react with simple electrophiles, these aminoquinones did react with haloquinones and also with unsubstituted quinones under very mild conditions to afford diquinonylamines in average to good yields. These vinylogous quinone-imides were characterized using common spectroscopic methods as well as X-ray crystallography.