Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 19, Pages 3605-3609Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob00745d
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Funding
- Welch Foundation [AX-1788]
- NSF [CHE-1455061]
- NIGMS [SC3GM105579]
- Max and Minnie Tomerlin Voelcker Fund
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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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