Novel Polycyclic Dianions: Metal Reduction of Nitrogen Heterocycles

Abraham Minsky, Yoram Cohen, Mordecai Rabinovitz*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Fused benzenoid heterocyclic systems, i.e., benzo(c)cinnoline (3), dibenzo(a, c) phenazine (4), and quinoxaline derivatives 5 and 6, were reduced with lithium and sodium in ether solvents to the corresponding antiaromatic doubly charged species. These dianions represent a new class of charged species, i.e., nitrogen-containing polycyclic anions. The 1H and 13C NMR spectra as well as theoretical calculations are reported and discussed in terms of antiaromatic contributions as well as the modes of interaction between the organic moiety and the cations. In view of the strong dependency of the 1H NMR spectra on the countercation and temperature, an equilibrium between ionic and covalent structure is suggested.

Original languageEnglish
Pages (from-to)1501-1505
Number of pages5
JournalJournal of the American Chemical Society
Issue number6
StatePublished - Mar 1985
Externally publishedYes


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