Download PDF
Synthesis 1974; 1974(6): 383-419
DOI: 10.1055/s-1974-23326
review
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of Carbocyclic Spiro Compounds via Intramolecular Alkylation Routes

A. Paul KRAPCHO*
  • *Department of Chemistry, University of Vermont, Burlington, Vermont 05401, U.S.A.
Further Information

Publication History

Publication Date:
20 October 2004 (online)

  PDF Download  Permissions and Reprints All articles of this category

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