Accelerated electrocyclic ring-opening of benzocyclobutenes under the influence of a beta-silicon atom
Yuji Matsuya1, Noriko Ohsawa, Hideo Nemoto
1Faculty of Pharmaceutical Sciences, University of Toyama, Japan.
Journal of the American Chemical Society
|January 13, 2006
Abstract:
A significant acceleration effect of a beta-silicon atom was observed on the electrocyclic ring-opening reaction of benzocyclobutene derivatives to form o-quinodimethanes. This acceleration effect could be attributed to an electronic sigma-donating nature of the C(alpha)-Si(beta) bond, associated with alpha-anion driven pericyclic reactions.
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