A Study of Valence Tautomerism of Cycloheptatriene-Norcaradiene

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Abstract
Rates of the Diels-Alder reaction of cycloheptatriene, tricyclo[4.3.1.0]deca-2,4-diene, 1,3-cyclohexadiene, and cis-bicyclo[4.3.0]nona-2,4-diene with excess of fumaryl chloride were measured using a dilatometer. Comparison of the rate of cycloheptatriene with that of other olefins raises the question of the free energy difference so far estimated between cycloheptatriene and norcaradiene, which has been proposed to exist in equilibrium. It is suggested that the most preferable mechanism of the Diels-Alder reaction of cycloheptatriene is not through the norcaradiene isomer, but through the transition state of the norcaradiene structure.

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