1,3-Diphenylbenzo[c]furan dianion: nuclear magnetic resonance characterization of a 4n? heterocyclic dianion containing oxygen

Yoram Cohen, Joseph Klein, Mordecai Rabinovitz
1988 Journal of the Royal Society of Chemistry, Perkin Transactions 2  
The metal reduction of 1,3-diphenylbenzo[c]furan (1) t o the corresponding dianion (I2-) has been carried out by alkali-metals. A detailed (1 D and 2D) n.m.r. investigation of (12-) enables characterization of its charge distribution as well as its spatial structure. The spectra of (I2-) 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
more » ... g experiments of the salts of (I2-). The reduction process induces in (I2-) a very high energy barrier for the rotation of the phenyl substituents.
doi:10.1039/p29880000031 fatcat:jh7hqjdh3rgcrlybglvwr6kieu