Cyclic Sulfites and Cyclic Sulfates: Epoxide like Synthons

Braj B. Lohray

doi:10.1055/s-1992-26295

Synthesis 1992; 1992(11): 1035-1052
DOI: 10.1055/s-1992-26295

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Cyclic Sulfites and Cyclic Sulfates: Epoxide like Synthons

Braj B. Lohray^*

^*Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India

Abstract

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This article reviews the recent developing synthetic utilities of cyclic sulfites and cyclic sulfates in organic chemistry, which rival in reactivity and selectivity with their very well studied friend, the epoxides and in many cases, are found to be superior to them. 1. Introduction 2. Structure 3. Synthesis of Cyclic Sulfites 4. Synthesis of Cyclic Sulfates 5. Reactivity 5.1. Thermal Rearrangement 5.2. Photochemical Rearrangement 5.3. Reaction with Electrophiles 5.3.1.Reaction with Acids 5.3.2.Electrophilic Addition to Double Bonds 5.4. Reaction with Nucleophiles 5.4.1.O-Nucleophiles 5.4.2.S-Nucleophiles 5.4.3. Halide Nucleophiles 5.4.4.C-Nucleophiles 5.4.5. N-Nucleophiles 5.4.6. H-Nucleophiles 5.5. Reaction with Radicals 5.6. Electrochemical Reduction of Cyclic Sulfates 6. Application in Research and Industry 7. Biological Activities 8. Conclusion

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