Decorated Cyclopentadienes from Acetylene and Ketones in Just Two Steps

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 rearrange...

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Veröffentlicht in:Organic letters 2017-06, Vol.19 (12), p.3127-3130
Hauptverfasser: Schmidt, Elena Yu, Bidusenko, Ivan A, Ushakov, Igor’ A, Vashchenko, Alexander V, Trofimov, Boris A
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01254