Reaction of 2,5-Dimethylfuran with Ethyl Propiolate: The Chemistry of Ethyl 1,4-Dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2-carboxylate

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Abstract
Thermal reaction of 2,5-dimethylfuran (1) and ethyl propiolate (2) affords the Diels–Alder adduct (3) and seven additional products, all of which are derived from 3. The major products, depending on the conditions, are the endo-exo 2:1 diadducts (4 and 5) and two nortricyclenes (8 and 10). The last two products arise by homo Diels–Alder type dimerization of 3 (to give 10) and subsequent Diels–Alder retrogression (to give 8). The minor reaction products include a third nortricyclene (9), isomeric with 8.

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