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 |
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ASJC Scopus subject areas
- Chemistry(all)
Cite this
Structure and dynamic stereochemistry of trimesitylmethane. I. Synthesis and nuclear magnetic resonance studies. / Finocchiaro, Paolo; Gust, John Devens; Mislow, Kurt.
In: Journal of the American Chemical Society, Vol. 96, No. 7, 1974, p. 2165-2167.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Structure and dynamic stereochemistry of trimesitylmethane. I. Synthesis and nuclear magnetic resonance studies
AU - Finocchiaro, Paolo
AU - Gust, John Devens
AU - Mislow, Kurt
PY - 1974
Y1 - 1974
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0001524227&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0001524227&partnerID=8YFLogxK
M3 - Article
VL - 96
SP - 2165
EP - 2167
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 7
ER -