Decorated Cyclopentadienes from Acetylene and Ketones
in Just Two Steps

Schmidt, Elena
Yu.; Bidusenko, Ivan A.; Ushakov, Igor’ A.; Vashchenko, Alexander V.; Trofimov, Boris A.

doi:10.1021/acs.orglett.7b01254.s001

ol7b01254_si_001.pdf (4.36 MB)

Decorated Cyclopentadienes from Acetylene and Ketones in Just Two Steps

journal contribution

posted 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.