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

被引：17

作者：

Kelly, Christopher B. ^{[1
]}

Colthart, Allison M. ^{[1
]}

Constant, Brad D. ^{[1
]}

Corning, Sean R. ^{[1
]}

Dubois, Lily N. E. ^{[1
]}

Genovese, Jacqueline T. ^{[1
]}

Radziewicz, Julie L. ^{[1
]}

Sletten, Ellen M. ^{[1
]}

Whitaker, Katherine R. ^{[1
]}

Tilley, Leon J. ^{[1
]}

机构：

[1] Stonehill Coll, Dept Chem, Easton, MA 02357 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 07期

关键词：

NEIGHBORING-GROUP PARTICIPATION; SILICON STABILIZATION; CARBONIUM-IONS; SOLVOLYSIS; TRIFLUOROMETHYL; CARBOCATIONS;

D O I：

10.1021/ol200121f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1646 / 1649

页数：4

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