L. Chaker et al., STUDIES ON THE OXIDATIVE ADDITION OF N,N-DIMETHYLAMINE TO BROMOJUGLONES AND BROMOMETHYLJUGLONES, Chemical and Pharmaceutical Bulletin, 42(11), 1994, pp. 2238-2240
The nucleophilic addition of dimethylamine to bromojuglones and bromom
ethyljuglones is followed by elimination of hydrogen bromide or oxidat
ion. With 2-bromojuglone, the oxidative process predominates at low te
mperature. The regiochemistry of the addition is a function of the tem
perature and of the position of the bromine atom (C-2 or C-3) on the q
uinone.