Benzocyclobutene radical anion

Reuben D. Rieke, Steve E. Bales, Phillip M. Hudnall, Claude F. Meares

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


The radical anion of benzocyclobutene was prepared by metal and electrolytic reduction. Conclusive evidence is presented showing the fused, four-membered ring remains intact after reduction. An interesting temperature dependence was noted for the epr spectra of the metal-reduced benzocyclobutene. At low temperatures, the four methylene protons are nonequivalent but become equivalent as the temperature is raised. This phenomenon is discussed in terms of an ion pairing process. Finally, the effect of ring strain on spin densities and reduction potentials is discussed.

Original languageEnglish (US)
Pages (from-to)697-703
Number of pages7
JournalJournal of the American Chemical Society
Issue number3
StatePublished - 1971
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)


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