Density functional theory computational study on Diels–Alder reactions of cyclopentadiene with selected vinylsilanes and methylenecyclopropane Academic Article uri icon

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abstract

  • Aimed at predicting relative reactivities, density functional theory (DFT) calculations were carried out on a series of Diels–Alder reactions involving silylvinyl derivatives reacting with cyclopentadiene as part of a synthetic research project. Using three reactions for which experimental rate data are available to calibrate our calculations, we computationally pinpointed the best synthetic route to bicyclo[2.2.1]hept-5-ene-2,2-diylbis(trimethylsilane) (1). The synthesis begins with the Diels–Alder reaction of cyclopentadiene (2) with commercially available (1-bromovinyl)trimethylsilane (6).

publication date

  • February 2011