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

Paolo Finocchiaro; Devens Gust; Kurt Mislow

doi:10.1021/ja00814a028

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

Paolo Finocchiaro, Devens Gust, Kurt Mislow

Molecular Sciences, School of (SMS)

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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 language	English (US)
Pages (from-to)	2165-2167
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	96
Issue number	7
DOIs	https://doi.org/10.1021/ja00814a028
State	Published - Apr 1 1974

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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.",

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AU - Gust, Devens

AU - Mislow, Kurt

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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.

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

Abstract

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