Stereochemistry of Dimesityl-9-anthrylmethane and Bis(2,6-xylyl)-1-(2-methylnaphthyl)methane. Evidence for the Two-Ring Flip Mechanism in Triarylmethanes

Paolo Finocchiaro, Devens Gust, Kurt Mislow

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

The temperature-dependent 1H-nmr spectra of the title compounds indicate that these molecules adopt a propeller conformation in the ground state, and that a variety of interconversions of stereoisomeric molecules on the nmr time scale occurs at elevated temperatures. These interconversions are all shown to proceed by the tworing flip mechanism. The associated free energies of activation are reported. Comparison of the present results with the results of earlier studies on triarylmethanes, triarylboranes, and cognates brings to light that the two-ring flip mechanism is the favored stereoisomerization pathway for all of these systems.

Original languageEnglish (US)
Pages (from-to)2176-2182
Number of pages7
JournalJournal of the American Chemical Society
Volume96
Issue number7
DOIs
StatePublished - Apr 1 1974

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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