5 years ago

Decorated Cyclopentadienes from Acetylene and Ketones in Just Two Steps

Decorated Cyclopentadienes from Acetylene and Ketones in Just Two Steps
Igor’ A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov, Ivan A. Bidusenko, Alexander V. Vashchenko
The products of the one-pot assembly of acetylene and ketones in the KOH/DMSO system, 7-methylene-6,8-dioxabicyclo[3.2.1]octanes, undergo an acid-catalyzed (CF3COOH, room temperature) rearrangement to rarely substituted cyclopentadienes in good-to-excellent yields. The mechanism of the rearrangement has been supported by the isolation and corresponding transformations of two intermediates.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01254

DOI: 10.1021/acs.orglett.7b01254

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