Charge migration in dicationic electrophiles and its application to the synthesis of aza-polycyclic aromatic compounds.
[reaction: see text] Superacid-promoted reactions of dicationic electrophiles have been studied, and the positive charge centers are found to migrate apart in a predictable manner. Using isotopic labeling the charge migration is found in one system to occur through successive deprotonation-reprotonation steps. The charge migration chemistry is the basis for new general synthetic route to aza-polycyclic aromatic compounds.
Li
Ang
A
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
Kindelin
Patrick J
PJ
Klumpp
Douglas A
DA
D001372:Aza Compounds / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D004563:Electrochemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*
D001372:Aza Compounds; D006571:Heterocyclic Compounds; D011084:Polycyclic Aromatic Hydrocarbons