1,3-diphenylbenzo[c]furan dianion: Nuclear magnetic resonance characterization of a 4nπ heterocyclic dianion containing oxygen

Yoram Cohen, Joseph Klein*, Mordecai Rabinovitz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)31-38
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number1
DOIs
StatePublished - 1988
Externally publishedYes

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