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James H. Rigby

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Name: Rigby, James H.
Organization: Wayne State University , USA
Department: Department of Chemistry
Title: Professor(PhD)

TOPICS

Entry into the homotriquinacene ring system via a silyl directed, acid catalyzed rearrangement of a 11-trimethylsilyl-tetracyclo[8.1.0.03,7.04,11]undeca-5,8-diene ring system
Co-reporter:Saptarshi De, Zeinab Shafie-Khorassani, James H. Rigby
Tetrahedron Letters 2013 Volume 54(Issue 10) pp:1208-1210
Publication Date(Web):6 March 2013
DOI:10.1016/j.tetlet.2012.12.050
A novel, acid catalyzed rearrangement of the 11-trimethylsilyl-tetracyclo[8.1.0.03,7.04,11]undeca-5,8-diene ring system was observed. The trimethylsilyl substitution on the cyclopropane moiety was found to be crucial for rapid, high yielding formation of the unusual homotriquinacene ring system. The transformation is presumed to proceed via a series of carbenium ion intermediates that can be trapped with suitable nucleophiles.
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