TY - JOUR
T1 - 1,3-diphenylbenzo[c]furan dianion
T2 - Nuclear magnetic resonance characterization of a 4nπ heterocyclic dianion containing oxygen
AU - Cohen, Yoram
AU - Klein, Joseph
AU - Rabinovitz, Mordecai
PY - 1988
Y1 - 1988
N2 - The metal reduction of 1,3-diphenylbenzo[c]furan (1) to the corresponding dianion (12-) has been carried out by alkali-metals. A detailed (1D and 2D) n.m.r. investigation of (12-) enables characterization of its charge distribution as well as its spatial structure. The spectra of (1 2-) differs when three alkalimetals are used for the reduction process. These differences are explained by an ion-solvation equilibrium which in turn explains the different stereoselectivity observed in the quenching experiments of the salts of (12-). The reduction process induces in (12-) a very high energy barrier for the rotation of the phenyl substituents.
AB - The metal reduction of 1,3-diphenylbenzo[c]furan (1) to the corresponding dianion (12-) has been carried out by alkali-metals. A detailed (1D and 2D) n.m.r. investigation of (12-) enables characterization of its charge distribution as well as its spatial structure. The spectra of (1 2-) differs when three alkalimetals are used for the reduction process. These differences are explained by an ion-solvation equilibrium which in turn explains the different stereoselectivity observed in the quenching experiments of the salts of (12-). The reduction process induces in (12-) a very high energy barrier for the rotation of the phenyl substituents.
UR - http://www.scopus.com/inward/record.url?scp=0006556202&partnerID=8YFLogxK
U2 - 10.1039/P29880000031
DO - 10.1039/P29880000031
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AN - SCOPUS:0006556202
SN - 1472-779X
SP - 31
EP - 38
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 1
ER -