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Site- and Regioselectivity of Nitrile Oxide–Allene Cycloadditions: DFT-Based Semiquantitative Predictions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-13 00:00:00 , DOI: 10.1021/acs.joc.7b01866 Giorgio Molteni 1 , Alessandro Ponti 2
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-13 00:00:00 , DOI: 10.1021/acs.joc.7b01866 Giorgio Molteni 1 , Alessandro Ponti 2
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Nitrile oxide 1,3-dipolar cycloaddition to arylsulfonyl- and dialkylaminoallenes have been investigated within the framework of the Kohn–Sham density functional theory (DFT) at the B3LYP/6-31G(d,p) level. The hitherto-unexplained experimental behavior of sulfonylallenes was rationalized by transition-state calculations which enabled a semiquantitative treatment of the cycloaddition site- and regioselectivity. The reliability of DFT computations was further established by predicting the complete selectivity of the nitrile oxide cycloaddition to dialkylaminoallenes according to previous experimental findings.
中文翻译：
氧化亚氮-丙二烯环加成反应的位点和区域选择性：基于DFT的半定量预测
在Kohn-Sham密度泛函理论（DFT）的框架内，在B3LYP / 6-31G（d，p）水平上已研究了将氧化腈1,3-偶极环加成至芳基磺酰基-和二烷基氨基烯丙基。通过过渡态计算合理化了迄今无法解释的磺腈的实验行为，该过渡态计算可以对环加成位点和区域选择性进行半定量处理。DFT计算的可靠性是根据先前的实验结果通过预测丁腈环氧化物对二烷基氨基丙二烯的完全选择性来进一步确定的。
更新日期：2017-09-13
中文翻译：
氧化亚氮-丙二烯环加成反应的位点和区域选择性：基于DFT的半定量预测
在Kohn-Sham密度泛函理论（DFT）的框架内，在B3LYP / 6-31G（d，p）水平上已研究了将氧化腈1,3-偶极环加成至芳基磺酰基-和二烷基氨基烯丙基。通过过渡态计算合理化了迄今无法解释的磺腈的实验行为，该过渡态计算可以对环加成位点和区域选择性进行半定量处理。DFT计算的可靠性是根据先前的实验结果通过预测丁腈环氧化物对二烷基氨基丙二烯的完全选择性来进一步确定的。
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