Journal
ORGANIC LETTERS
Volume 13, Issue 7, Pages 1646-1649Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol200121f
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- Stonehill College
- Office of Naval Research [N0014-08-1-1160]
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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 gamma-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.
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