TY - JOUR
T1 - Novel Polycyclic Dianions
T2 - Metal Reduction of Nitrogen Heterocycles
AU - Minsky, Abraham
AU - Cohen, Yoram
AU - Rabinovitz, Mordecai
PY - 1985/3
Y1 - 1985/3
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0000191044&partnerID=8YFLogxK
U2 - 10.1021/ja00292a009
DO - 10.1021/ja00292a009
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AN - SCOPUS:0000191044
SN - 0002-7863
VL - 107
SP - 1501
EP - 1505
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 6
ER -