d-orbital stereoelectronic control of the stereochemistry of SN2′ displacements by organocuprate reagents |
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Authors: | EJ Corey Neil W Boaz |
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Institution: | Department of Chemistry, Harvard University, Cambridge, Massachusetts 02138 U.S.A. |
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Abstract: | The stereochemistry observed in organocuprate SN2′ displacements can be rationalized as a stereoelectronic effect arising from “bidentate” binding involving a d orbital of nueleophilic copper and π* and σ* orbitals of the substrate. The extension of this idea to other reactions of organocuprates including additions to acetylenes and enones is discussed. |
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