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Synthesis 1974; 1974(6): 383-419
DOI: 10.1055/s-1974-23326
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Synthesis of Carbocyclic Spiro Compounds via Intramolecular Alkylation Routes

A. Paul KRAPCHO*
  • *Department of Chemistry, University of Vermont, Burlington, Vermont 05401, U.S.A.
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Publication Date:
20 October 2004 (online)

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Intramolecular alkylation processes which lead to the formation of compounds with a free carbocyclic spiro linkage are reviewed. 1. Intramolecular Dehydrohalogenations, Dehydrotosylations, and Related Reactions 1.1. 2-(ω-Bromoalkyl)cycloalkanones 1.2. Detosylations of Steroidal α,β-Unsaturated Ketones and β,γ-Unsaturated Cyclohexenones 1.3. 9-(ω-Haloalkyl)fluorenes 1.4. α-Halo-β,β-cycloalkyl Glutaric Acids and Esters 1.5. Phenylspiropentane from the Deamination of a Quaternary Aminium Compound 1.6. Intramolecular Dehydration of 2-(2-Hydroxyethyl)cyclohexanone 1.7. Neighboring Group Participation Routes 2. Intermolecular Processes Followed by Intramolecular Dehydrohalogenations and Similar Cyclizations 2.1. Di- and Tetraalkylations of Ketonic Substrates with α,ω-Dihaloalkanes 2.2. Treatment of Dimedone with β-Acetoxyethylmercury(II) Chloride 2.3. Guareschi Imide Dialkylations 2.4. Dialkylations of Compounds with Non-Ketonic Active Methylene Groups 2.5. Intermolecular Displacements Followed by Cyclizations 2.6. Michael Additions Followed by Intramolecular Eliminations 2.7. α,α′ -Annelation Processes- Enamine Alkylations Followed by Michael Reaction 2.8. Michael Additions 3. Intramolecular Dehalogenations and Related Reactions 3.1. Reductions Leading to Spiropentanes 3.2. Reductions Leading to Spirocyclopropyl Systems 3.3. Reductions Leading to Spirocyclopropyl Ketones 3.4. Reductions of α,α′-Dihaloketones 3.5. Reductive Cyclizations of Guareschi Imide Dibromides 3.6. α,α′-Dibromo-β,β-cycloalkyl Glutaric Esters 4. Free Radical Cyclizations 4.1. Oxidative Phenol Couplings 4.2. Oxidative Couplings of Methylene-bis-dimedones 4.3. Radical Cyclizations at Double Bonds 4.4. Substituted Difluorenol Coupling 4.5. Photochemical Dehydrobrominations 5. Acid-Catalyzed Cyclizations 5.1. Cyclodehydrations of Alcohols 5.2. Unsaturated Substrate Cyclizations 5.3. Intermolecular Acid-Catalyzed Cyclizations Followed by Intramolecular Cyclizations 6. Thermal Cyclizations 6.1. Conia Cyclizations 6.2.Thermal and Photochemical Decomposition of Spiro Pyrazoline Adducts

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