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Issue 19, 2018
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Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent

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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.

Graphical abstract: Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent

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Publication details

The article was received on 30 Mar 2018, accepted on 23 Apr 2018 and first published on 23 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00745D
Citation: Org. Biomol. Chem., 2018,16, 3605-3609
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    Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent

    H. T. Dang, V. T. Nguyen, V. D. Nguyen, H. D. Arman and O. V. Larionov, Org. Biomol. Chem., 2018, 16, 3605
    DOI: 10.1039/C8OB00745D

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