Abstract
The rearrangement reactions of silylated alcohols bearing the highly strained structures of cyclopropene and cyclopropanol connected in adjacent positions have been studied under ZnI2- and Rh(I)-catalyzed conditions. The results show intriguing carbon skeletal reorganizations of such system under these conditions. The ZnI2-catalyzed reaction proceeds with C-O cleavage and the rearrangement of the resultant carbon cation, leading to the breaking of the C-C single bond that connects two three-memebered rings. In contrast, the Rh(I)-catalyzed reaction involves σ-bond oxidative addition of the cyclopropene moiety, followed by β-carbon elimination of the cyclopropane moiety.
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