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2-Bromo[6]helicene as a Key Intermediate for [6]Helicene Functionalization
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-03-13 00:00:00 , DOI: 10.1021/acs.joc.7b03234
Martin Jakubec 1 , Tomáš Beránek 1 , Pavel Jakubík 1 , Jan Sýkora 1 , Jaroslav Žádný 1 , Vladimír Církva 1 , Jan Storch 1
Affiliation  

The synthesis of 2-bromo[6]helicene was revised and improved up to 51% yield. Its reactivity was thoroughly investigated, and a library of 17 different carbon, boron, nitrogen, phosphorus, oxygen and sulfur substituted derivatives was prepared. The racemization barrier for 2-bromo[6]helicene was determined, and the usage of enantiomers in the synthesis of optically pure helicenes was rationalized. The three most energy-demanding reactions using enantiomerically pure 2-bromo[6]helicene were tested in order to confirm the predicted enantiomeric excess.

中文翻译:

2-溴[6]螺旋烯为[6]螺旋烯官能化的关键中间体

修订了2-溴[6]螺旋烯的合成方法,并将其产率提高到51%。对其反应性进行了彻底研究,并制备了一个由17种不同的碳,硼,氮,磷,氧和硫取代的衍生物组成的库。确定了2-溴[6]螺旋的外消旋化障碍,并合理化了对映异构体在光学纯螺旋烯的合成中的使用。测试了使用对映体纯的2-溴[6]螺旋烯的三个最需要能量的反应,以确认预测的对映体过量。
更新日期:2018-03-13
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