Structure and Dynamic Stereochemistry of Trimesitylmethane. I. Synthesis and Nuclear Magnetic Resonance Studies

Paolo Finocchiaro, Devens Gust, Kurt Mislow

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

Trimesitylmethane, a sterically congested molecule, has been synthesized in low yield, and the temperature dependence of its 1H-nmr spectrum has been studied. The molecule assumes a propeller conformation in the ground state, and the barrier for interconversion of enantiomeric propellers by the two-ring flip mechanism is ΔG 167 = 21.9 kcal/mol. This remarkably high barrier admits the possibility of resolution of 1 under ordinary conditions.

Original languageEnglish (US)
Pages (from-to)2165-2167
Number of pages3
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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