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The scope and utility of the metal-catalyzed rearrangement of propargyl acetates first reported by Rautenstrauch were expanded. Treatment of a series of appropriate acetate substrates with Pd(II)- and Hg(II)-catalysts afforded synthetically useful fused 5,6-bicyclic-1,4-cyclopentadienyl acetates and 2-cyclopentenones. It was found that the substituents at the terminal alkynyl and alkenyl positions...
Furans and benzofurans of type 1 were dearomatized via the [2,3]-Still–Wittig rearrangement. Enol ethers 2 could be isolated or isomerized to the corresponding furans 3. The substitution pattern at the homofuranylic position had a strong influence on reaction behavior. Benzofurans rearranged with the greatest efficiency, and employment of a 3-substituted benzofuran (1; R′=CH 3 ) allowed the...
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