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

Paolo Finocchiaro; John Devens Gust; Kurt Mislow

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

Paolo Finocchiaro, John Devens Gust, Kurt Mislow

Arizona State University

Research output: Contribution to journal › Article › peer-review

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 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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title = "Structure and dynamic stereochemistry of trimesitylmethane. I. Synthesis and nuclear magnetic resonance studies",

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.",

author = "Paolo Finocchiaro and Gust, {John Devens} and Kurt Mislow",

year = "1974",

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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.

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