期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 16, 期 19, 页码 3605-3609出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob00745d
关键词
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资金
- Welch Foundation [AX-1788]
- NSF [CHE-1455061]
- NIGMS [SC3GM105579]
- Max and Minnie Tomerlin Voelcker Fund
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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