Equilibrium and kinetic deuterium isotope effects on the hetero-Diels-Alder addition of sulfur dioxide

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Abstract

The C-S bond is formed to a greater extent than the C-O bond in the transition state of the [4+2] cycloaddition of S02 to dimethylidenecyclohexane (see scheme). Both deuterium isotope effects and quantum calculations lead to this conclusion.

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Monnat, F., Vogel, P., Meana, R., & Sordo, J. A. (2003). Equilibrium and kinetic deuterium isotope effects on the hetero-Diels-Alder addition of sulfur dioxide. Angewandte Chemie - International Edition, 42(33), 3924–3927. https://doi.org/10.1002/anie.200351732

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