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.
|Number of pages||8|
|Journal||Journal of the Chemical Society, Perkin Transactions 2|
|State||Published - 1988|