ol7b01254_si_001.pdf (4.36 MB)
Decorated Cyclopentadienes from Acetylene and Ketones in Just Two Steps
journal contributionposted on 2017-05-26, 18:51 authored by Elena Yu. Schmidt, Ivan A. Bidusenko, Igor’ A. Ushakov, Alexander V. Vashchenko, Boris A. Trofimov
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.