ArticleOrganic & biomolecular chemistry2018
Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent.
Article in Organic & biomolecular chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed, 27 citations in OpenAlex.
- Alkali-Metal Base Catalyzed Electrocyclization of Isoprene Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- The Latest Progress in the Chemistry ofMolecules (Basel, Switzerland) · 2024Review
- Catalytic Dienylation: An Emergent Strategy for the Stereoselective Construction of Conjugated Dienes and Polyenes.Synthesis · 2023Article
- Copper-Catalyzed Stille Cross-Coupling Reaction and Application in the Synthesis of the Spliceostatin Core Structure.The Journal of organic chemistry · 2020Article
- Highly Stereoselective and Catalytic Desulfitative C-O and C-I Dienylation with Sulfolenes: the Importance of Basic Additives.Tetrahedron · 2019Article
- Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.Journal of the American Chemical Society · 2018Article
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Authors and funding
5 authors at 1 institution in 1 country.
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Abstract
We present herein an efficient and practical method for a gram scale synthesis of 3-sulfolenes using sodium metabisulfite as a safe, inexpensive, and easy to handle sulfur dioxide equivalent. Diversely-substituted 3-sulfolenes can be prepared by reacting a variety of 1,3-dienes or allylic alcohols with sodium metabisulfite in aqueous hexafluoroisopropanol (HFIP) or in aqueous methanol in the presence of potassium hydrogen sulfate. Advantageously, the method enables conversion of allylic alcohols directly to 3-sulfolenes, bypassing intermediate 1,3-dienes.
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