Acid-catalyzed rearrangements of tricyclo[4.3.2]Propellane derivatives |
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| Authors: | Amos B. Smith Barry A. Wexler |
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| Affiliation: | Department of Chemistry, The Laboratory for Research on the Structure of Matter, and The Monell Chemical Senses Center, The University of Pennsylvania, Philadelphia, Pennsylvania, 19104 U.S.A. |
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| Abstract: | The acid-catalyzed rearrangements of three model tricyclo[4.3.2] propellane derivatives have been explored. In each case the observed products are proposed to arise via a concerted 1,2-shift of the cyclobutane bond having an antiperiplanar alignment with the leaving group (i.e., stereoelectronic control). |
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