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

Autor:	Leon J. Tilley, Allison M. Colthart, Lily N. E. Dubois, Katherine R. Whitaker, Julie L. Radziewicz, Brad D. Constant, Sean R. Corning, Christopher B. Kelly, Jacqueline T. Genovese, Ellen M. Sletten
Rok vydání:	2011
Předmět:	Silylation Stereochemistry Chemistry Group (periodic table) Organic Chemistry Cationic polymerization Physical and Theoretical Chemistry Carbocation Biochemistry
Zdroj:	Organic Letters. 13:1646-1649
ISSN:	1523-7052 1523-7060
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d830e4dda2abd6c2f9218c964fb7c234 https://doi.org/10.1021/ol200121f Zobrazit plný text záznamu