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 language | English |
|---|---|
| Pages (from-to) | 2165-2167 |
| Number of pages | 3 |
| Journal | Journal of the American Chemical Society |
| Volume | 96 |
| Issue number | 7 |
| Publication status | Published - 1974 |
ASJC Scopus subject areas
- Chemistry(all)
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Finocchiaro, P., Gust, J. D., & Mislow, K. (1974). Structure and dynamic stereochemistry of trimesitylmethane. I. Synthesis and nuclear magnetic resonance studies. Journal of the American Chemical Society, 96(7), 2165-2167.