Journal of Organic Chemistry p. 5460 - 5464 (1988)
Update date:2022-08-11
Topics:
Sera, Akira
Ohara, Meguru
Kubo, Toshiaki
Itoh, Kuniaki
Yamada, Hiroaki
et al.
The Diels-Alder reaction of furan with dialkyl (acetoxymethylene)malonates 1 did not proceed even in the presence of Lewis acid catalysts under conventional conditions.However, the reaction under high pressure (1.1 GPa) gave the expected cycloadducts, dialkyl 3-acetoxy-7-oxabicyclo<2.2.1>hept-5-ene-2,2-dicarboxylates 2.The bis-, tris-, and tetrakisadducts 3-6 were also produced in some amounts.Similar high-pressure reactions in the presence of zinc iodide as a catalyst yielded dialkyl 2-furfurylidenemalonate 8, and none of the adducts were obtained.
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