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CAN Mediated Reaction of Aryl Sulfinates with Alkenes and Alkynes: Synthesis of Vinyl Sulfones, β-Iodovinyl Sulfones and Acetylenic Sulfones

Vijay Nair*, Anu Augustine, T. D. Suja

*Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum-695 019, India, Email: gvncsrrltrd.ren.nic.in

V. Nair, A. Augustine, T. D. Suja, Synthesis, 2002, 2259-2265.

DOI: 10.1055/s-2002-34838


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Abstract

The cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent a similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate afforded the corresponding acetylenic sulfones in high yields.

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   proposed mechanism



Key Words

cerium(IV) ammonium nitrate, sulfonylation, aryl alkenes, alkenes, acetylenes, vinyl sulfones, β-iodovinyl sulfones, acetylenic sulfones


ID: J66-Y2002-1520