The Catalysis Center for Energy Innovation at UD has reported a green route to p-xylene, which involves Diels-Alder addition of ethylene to biomass-derived dimethylfuran. However, computational studies suggested that the Diels-Alder reaction is not catalyzed. (Scheme 1) Even though dimethyl-oxa-norbornene is widely accepted as the intermediate of the reaction, it has never been synthesized, isolated or fully characterized. The synthesis of dimethyl-oxa-norbornene will enable a search for a catalyst for the retro-Diels-Alder reaction. By the principle of microscopic reversibility, such a catalyst would also facilitate the forward-Diels-Alder reaction. We have made some progress synthesizing dimethyl-oxa-norbornene. Due to the instability of oxa-norbornene and derivatives, we are trying to stabilize the desired dimethyl-oxa-norbornene intermediate as a transition metal complex. (Scheme 2) These synthetic studies also inspired us to search for alternative environmentally benign paths from dimethylfuran to p-xylene. More details will be presented and discussed in the presentation.

Synthesis of dimethyl-oxa-norbornene and alternative paths from dimethylfuran to p-xylene

253rd National Meeting (2017)

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