- 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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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.
- Dang, Hang T.,Nguyen, Vu T.,Nguyen, Viet D.,Arman, Hadi D.,Larionov, Oleg V.
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supporting information
p. 3605 - 3609
(2018/05/26)
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- Stoichiometric release of SO2 from adducts: Application to the direct synthesis of protected dienes
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Abstract The in situ, stoichiometric release of SO2 was studied from DABSO (DABCO adduct with SO2) and DMAP adduct. When involved in cheletropic additions, free SO2 released by this technique proved much more reactive than its adducts. Some examples of applications towards the direct synthesis of protected dienes from allylic alcohols are given.
- Martial, Ludovic,Bischoff, Laurent
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supporting information
p. 1225 - 1229
(2015/06/02)
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