Structure and dynamic stereochemistry of trimesitylmethane. I. Synthesis and nuclear magnetic resonance studies

Paolo Finocchiaro, John Devens Gust, Kurt Mislow

Research output: Contribution to journalArticle

58 Citations (Scopus)

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
Pages (from-to)2165-2167
Number of pages3
JournalJournal of the American Chemical Society
Volume96
Issue number7
Publication statusPublished - 1974

    Fingerprint

ASJC Scopus subject areas

  • Chemistry(all)

Cite this