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Synthesis 1984; 1984(8): 629-656
DOI: 10.1055/s-1984-30921
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Synthetically Useful Reactions of Epoxides

Janice Gorzynski Smith*
  • *Department of Chemistry, Mount Holyoke College, South Hadley, Massachusetts 01075, U.S.A.
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Publication History

Publication Date:
22 May 2002 (online)

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The synthetically useful reactions of epoxides are reviewed in this article. An emphasis is placed on methods which have recently been reported in the literature. 1. Introduction 2. Reaction of Epoxides with Nucleophiles 2.1. General Considerations 2.2. Ring Opening of Epoxides with Heteroatomic Nucleophiles 2.3. Ring Opening of Epoxides with Carbon Nucleophiles 2.4. Intramolecular Ring Opening of Epoxides 3. Rearrangement of Epoxides to Carbonyl Compounds 4. Rearrangement of Epoxides to Allylic Alcohols 5. Deoxygenation of Epoxides to Olefins 6. Reduction of Epoxides to Alcohols 7. Epoxides with Adjacent Functional Groups 7.1. Monoepoxides of 1,3-Dienes 7.2. α,β-Epoxyketones 7.3. α,β-Epoxysilanes 8. Conclusions