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Synthesis 1975; 1975(6): 347-357
DOI: 10.1055/s-1975-23755
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Preparative Aspects of Silver Ion-Catalyzed Rearrangements of Polycyclic Systems

Leo A. PAQUETTE*
  • *Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, U.S.A.
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Publication Date:
12 September 2002 (online)

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A survey is presented of the utilitarian role played by silver(I) ion in promoting synthetically useful rearrangements of polycyclic systems. The topics covered are (i) bicyclo[1.1.0]butane and bicyclo[2.1.0]pentane transformations, (ii) cyclopropene isomerizations, (iii) bond reorganizations of cubyl systems, and (iv) alkoxyl group ionization processes. 1. Bicyclo[1.1.0]butane Transformations 1.1. The Cyclohexene-1,3-Cycloheptadiene Ring Expansion 1.2. Formation of Bicyclo[3.2.0]hept-6-enes 1.3. Homologative Oxygenation of Cyclohexenes 2. The Bicyclo[2.1.0]pentane-Cyclopentene Isomerization 3. Cyclopropene Rearrangement Reactions 3.1. Ring Opening Processes 3.2. The Bicyclopropenyl - Dewar Benzene Rearrangement 4. Bond Reorganization of Cubyl Systems 4.1. Snoutene 4.2. Semibullvalenes 4.3. Annulated Semibullvalenes 5. Alkoxyl Group Ionizations and Epoxide Rearrangements