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Absence of the Thorpe-Ingold Effect by gem-Diphenyl Groups in Ring-Closing Enyne Metathesis
Authors:Kim Yi Jin  Grimm Jonathan B  Lee Daesung
Affiliation:a Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA
b Department of Chemistry, University of Wisconsin-Madison, WI 53706, USA
Abstract:In tandem ring-closing metathesis of alkynyl silaketals containing two different tethered olefins, the gem-dimethyl group showed the expected Thorpe-Ingold effect, thereby giving good level of group selectivity. Unexpectedly, however, the corresponding gem-diphenyl group did not show any Thorpe-Ingold effect for the ring-closure reaction.
Keywords:Thorpe-Ingold effect   Cyclization   Enyne metathesis   Ring-closing metathesis   Silicon
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