Kinetics,mechanism, and stereochemistry of Diels-Alder reactions of CN-substituted ethenes with cyclohexa-1, 3-diene in the gas phase |
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Authors: | B Van Mele G Huybrechts |
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Abstract: | The kinetics of the Diels-Alder additions of CH2 = CHCN, CH2 = C(CH3) CN, and cis- and trans-CH3CH = CHCN to cyclohexa-1, 3-diene have been studied in the gas phase. The stereochemistry of these reactions is discussed. In terms of a biradical mechanism, a minimum value of 4.1 ± 0.8 kcal mol?1 for the stabilizing effect of a CN group vis-à-vis a methyl group is shown to fit the experimental activation energies. |
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