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Electrophilic Cyclization of Phenylalkynediols to Naphthyl(aryl)iodonium Triflates with Chelating Hydroxyls: Preparation and X-ray Analyses
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-11 00:00:00 , DOI: 10.1021/acs.joc.7b01619 Robert J. Hinkle 1 , Sarah E. Bredenkamp 1 , Robert D. Pike 1 , Seong Ik Cheon 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-11 00:00:00 , DOI: 10.1021/acs.joc.7b01619 Robert J. Hinkle 1 , Sarah E. Bredenkamp 1 , Robert D. Pike 1 , Seong Ik Cheon 1
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Alkynediols containing one propargylic alcohol as well as a second alcohol, which is propargylic or homopropargylic, react with PhI+CN–OTf (Stang’s reagent) or 3,5-(CF3)2C6H3I+CN–OTf to afford naphthyl(aryl)iodonium triflates. The reaction occurs at room temperature over the course of 6–12 h and provides 36–82% yields of microcrystalline solids. Slow diffusion of Et2O into CH3CN solutions of the salts afforded X-ray quality crystals of five compounds with hydroxyl groups forming five- and six-membered chelation complexes with the iodine atom. Crystallizations from larger scale reactions (≥∼0.25 mmol) were generally facile from CH2Cl2.
中文翻译：
苯炔炔二醇与螯合羟基的亲电合成萘基（芳基）碘鎓三氟甲磺酸酯：制备和X射线分析
含有一种炔丙醇和另一种炔丙醇或均丙炔醇的炔二醇与PhI + CN - OTf（Stang's试剂）或3,5-（CF 3）2 C 6 H 3 I + CN - OTf反应制得萘基（芳基）碘鎓三氟甲磺酸。该反应在室温下进行6-12小时，可提供36-82％的微晶固体收率。Et 2 O缓慢扩散到CH 3中盐的CN溶液可提供五种带有羟基的化合物的X射线质量晶体，该化合物与碘原子形成五元和六元螯合配合物。大规模反应（≥〜0.25 mmol）的结晶通常易于从CH 2 Cl 2进行。
更新日期：2017-09-11
中文翻译：
苯炔炔二醇与螯合羟基的亲电合成萘基（芳基）碘鎓三氟甲磺酸酯：制备和X射线分析
含有一种炔丙醇和另一种炔丙醇或均丙炔醇的炔二醇与PhI + CN - OTf（Stang's试剂）或3,5-（CF 3）2 C 6 H 3 I + CN - OTf反应制得萘基（芳基）碘鎓三氟甲磺酸。该反应在室温下进行6-12小时，可提供36-82％的微晶固体收率。Et 2 O缓慢扩散到CH 3中盐的CN溶液可提供五种带有羟基的化合物的X射线质量晶体，该化合物与碘原子形成五元和六元螯合配合物。大规模反应（≥〜0.25 mmol）的结晶通常易于从CH 2 Cl 2进行。
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