Efficient synthesis of 3-sulfolenes from allylic alcohols and 1, 3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent. Issue 19 (27th April 2018)

• Record Type: Journal Article
• Authors: Dang, Hang T.; Nguyen, Vu T.; Nguyen, Viet D.; Arman, Hadi D.; Larionov, Oleg V.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 19(2018)
• Page Start: 3605
• Page End: 3609
• Publication Date: 2018-04-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00745d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The new method enables a simple and efficient synthesis of 3-sulfolenes from 1, 3-dienes and allylic alcohols using sodium metabisulfite. 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.