Solar driven uphill conversion of dicyclopentadiene to cyclopentadiene: an important synthon for energy systems and fine chemicals

摘要: The retro Diels–Alder conversion of endo-dicyclopentadiene to cyclopentadiene (Cp) – which is thermodynamically uphill under ambient conditions (ΔG = +9.7 kcal mol−1; values based on computation at 273 K following CBS-QB3 methodology) was carried out 175–190 °C in neat state using solar energy. reaction favorable elevated temperature. Considering heat release from the reverse (ΔH −23.4 mol−1), energy storage efficiency computed be ca. 5.5% with respect IR component concentrated radiation. Solar further utilized for preparation a model 2,5-norbornadiene derivative (75% isolated yield) through cycloaddition Cp 4-phenylbut-3-yn-2-one 150–185 °C. norbornadiene–quadricyclane system has been proposed storage, and its assisted synthesis would help reduce carbon footprint over life cycle. Norbornadiene may also interest greener processing fuels derived this compound. Cookson's cage ketone, too as an medium, additionally synthesized adduct p-benzoquinone employing photo-thermochemical conditions. proceeded rapidly (15 min) gave desired product 96% yield. Besides above applications, important synthon fine chemicals.