Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
High-Pressure Kinetics of the (6+4)π Cycloaddition of Tropone with 2,3-Dimethyl-1,3-butadiene, an Acyclic Diene. The Temperature and Solvent Effects
Shigeru SugiyamaHitoshi Takeshita
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1987 Volume 60 Issue 3 Pages 977-980

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Abstract

By a high-pressure kinetic analysis in isopropylbenzene, 1,4-dioxane and N,N-dimethylformamide, the activation parameters for the (6+4)π cycloaddition reaction of tropone with 2,3-dimethyl-1,3-butadiene were determined. The findings support the concerted nature for the Woodward–Hoffmann rule-allowed thermal addition reaction of tropone. A secondary orbital interaction, which was used to predict the correct stereochemistry of the adducts, exerted no effect on the volume profile.

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