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Synthesis 1978; 1978(2): 77-126
DOI: 10.1055/s-1978-24682
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Synthesis of Carbocyclic Spiro Compounds via Cycloaddition Routes

A. Paul KRAPCHO*
  • *Department of Chemistry, University of Vermont, Burlington, Vermont 05401, U.S.A.
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Publication Date:
12 September 2002 (online)

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Cycloaddition reactions which lead to the formation of compounds with a free carbocyclic spiro linkage are reviewed. The reactions are classified by the type of Cycloaddition process which is formally occurring in the spiroannelation stage. This article complements two previous reviews on the formation of carbocyclic spiro compounds via intramolecular alkylation1 and rearrangement2 routes. 1. α-Elimination Routes 1.1. Dihalo- and Halocarbene Cycloaddition Reactions 1.2. Alkoxy- and Ethoxycarbonylcarbenes 1.3. 2-Cyclohexenylidene 1.4. Cycloalkylidenes from Halogen-Metal Exchange Reactions of 1,1-Dihalides 1.5. Bis[trimethylstannyl]dihalomethanes Thermolysis in Cyclohexene 1.6. Diphenylcyclopropenylidene from O-Cyclopropenyl Carbamate 2. 1,3- and 1,5-Elimination Reactions of HX 2.1. Dimethylvinylidenecarbene 2.2. 3,5-Di-t-butyl-4-oxo-2,5-cyclohexadien-1-ylidene (1,5-Elimination) 3. Photolytic Decarboxylation to a Carbene 4. Simmons-Smith Type Cyclopropanation Reactions 4.1. Unsaturated Alcohols and Ethers 4.2. α-Allenic Alcohols 4.3. Allenes 4.4. Olefins 4.5. Ketones 4.6. α,β-Unsaturated Cyclic Ketones 5. Bis[bromomethyl]mercury Methylene Transfer Reactions 6. Atomic Carbon Reactions 7. Carbenes from Diazo Compounds 7.1. Diazomethane and Substituted Diazoalkanes 7.2. Alkoxycarbonylcarbene Cycloaddition Reactions 7.3. Cyclic Diazo Compounds 8. [2π+2π] Cycloaddition Reactions 8.1. Thermal Cyclodimerization Reactions 8.2. Thermal Crossed Cycloaddition Reactions 8.3. Allene Oligomerization Reactions 8.4. o-Quinonoid-Allene Cyclization Reactions 8.5. Metal-Catalyzed Reactions 8.6. Photocycloaddition Reactions 9. [4π+2π] Cycloaddition Reactions 9.1. Olefin to Diene 9.2. Diene to Substituted Exocyclic α,β-Unsaturated Ketones 9.3. Diene to α-Methylenecycloalkanones 9.4. Cyclodimerization Reactions of o-Quinonodimethane Intermediates 9.5. Cyclodimerization Reactions of 10-Methyleneanthrone 9.6. p-Quinone-Methide to Diene Adducts 9.7. Miscellaneous 6 Electron Cycloaddition Reactions 10. 8, 10, and 14π Electron Cycloaddition Reactions 10.1. [6π+2π] Cycloaddition Reactions 10.2. [8π+2π] Cycloaddition Reactions 10.3. [12π+2π] Cycloaddition Reactions