Enabling the Synthesis of Perfluoroalkyl Bicyclobutanes via 1,3 γ-Silyl Elimination

Two new bicyclobutanes were prepared from cyclobutyl systems by a novel, solvolytic, carbocation-based methodology. An electron-withdrawing perfluoroalkyl group at the incipient cationic center enhances neighboring-group participation of the γ-silyl group, inducing facile, remarkably selective 1,3-e...

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Veröffentlicht in:Organic letters 2011-04, Vol.13 (7), p.1646-1649
Hauptverfasser: Kelly, Christopher B, Colthart, Allison M, Constant, Brad D, Corning, Sean R, Dubois, Lily N. E, Genovese, Jacqueline T, Radziewicz, Julie L, Sletten, Ellen M, Whitaker, Katherine R, Tilley, Leon J
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Sprache:eng
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Zusammenfassung:Two new bicyclobutanes were prepared from cyclobutyl systems by a novel, solvolytic, carbocation-based methodology. An electron-withdrawing perfluoroalkyl group at the incipient cationic center enhances neighboring-group participation of the γ-silyl group, inducing facile, remarkably selective 1,3-elimination yielding only bicyclobutanes. The method unlocks potential access to a host of EWG-substituted strained rings and a potential new method for the synthesis of trifluoromethylcyclopropanes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200121f