NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes

NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes
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NBS/DMSO 介导的芳氧基甲基硫杂丙烷合成 (2,3-二氢苯并[b][1,4]氧噻啶-3-基)甲醇

DOI：
10.1039/c8nj01117f
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发表时间：
2018-05
期刊：
New Journal of Chemistry
影响因子：
3.3
通讯作者：
Xu Jiaxi
Xu Jiaxi
中科院分区：
化学3区
文献类型：
--
作者：
Dong Jun;Xu Jiaxi

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（2,3 - 二氢苯并[b][1,4]氧硫杂环己烯 - 3 - 基）甲醇是通过在微波辐射下，芳氧基甲基硫杂环丙烷与N - 溴代丁二酰亚胺（NBS）在二甲基亚砜（DMSO）中发生反应合成的。反应机理被认为是分子内芳香亲电取代……（原文此处“sub”不完整，推测应为“substitution”，完整意思为“取代反应” ）
(2,3-Dihydrobenzo[b][1,4]oxathiin-3-yl)methanols were synthesized via reactions of aryloxymethylthiiranes and N-bromosuccinimide (NBS) in DMSO under microwave irradiation. The reaction mechanism was proposed as an intramolecular aromatic electrophilic substitution of 1-bromo-2-(aryloxymethyl)thiiran-1-iums, generated from aryloxymethylthiiranes and NBS, and the subsequent DMSO nucleophilic ring opening reaction of thiiran-1-iums followed by the water displacement. The current method provides a direct and simple strategy in the efficient preparation of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from readily available aryloxymethylthiiranes.
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