Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
The Metalation of 1- and 2-(Trifluoromethyl)naphthalenes: Noteworthy Site Selectivities
Synthesis ( IF 2.2 ) Pub Date : 2005-02-09 , DOI: 10.1055/s-2005-861814 Manfred Schlosser , Fabrice Cottet , Eva Castagnetti
Synthesis ( IF 2.2 ) Pub Date : 2005-02-09 , DOI: 10.1055/s-2005-861814 Manfred Schlosser , Fabrice Cottet , Eva Castagnetti
This article provides insight into the various factors by which electroneg. substituents affect the kinetic acidity of arenes and, more specifically, naphthalenes. Both 1- and 2-(trifluoromethyl)naphthalenes were consecutively treated with an organometallic or lithium dialkylamide-type base and carbon dioxide. Due to single electron-transfer triggered side reactions, the yields of (trifluoromethyl)naphthoic acids were moderate to poor. 1-(Trifluoromethyl)naphthalene was exclusively attacked at the 2-position as expected. The 2-isomer reacted with tert-butyllithium in the presence of potassium tert-butoxide solely at the 1-position, but with sec-butyllithium in the presence of N,N,N',N'-tetramethylethylenediamine concomitantly at the 3- and 4-positions. Authentic samples of the key acids were prepd. based on independent, unambiguous methods. [on SciFinder (R)]
中文翻译:
1-和 2-(三氟甲基)萘的金属化:值得注意的位点选择性
这篇文章提供了对影响电子的各种因素的见解。取代基影响芳烃的动力学酸度,更具体地说,影响萘的动力学酸度。用有机金属或二烷基氨基锂型碱和二氧化碳连续处理 1-和 2-(三氟甲基)萘。由于单电子转移引发的副反应,(三氟甲基)萘甲酸的产率适中至差。正如预期的那样,1-(三氟甲基)萘仅在 2 位受到攻击。2-异构体在叔丁醇钾存在下仅在 1-位与叔丁基锂反应,但在 N,N,N',N'-四甲基乙二胺存在下与仲丁基锂同时在 3-和4个位置。制备了关键酸的正宗样品。基于独立、明确的方法。
更新日期:2005-02-09
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
1-和 2-(三氟甲基)萘的金属化:值得注意的位点选择性
这篇文章提供了对影响电子的各种因素的见解。取代基影响芳烃的动力学酸度,更具体地说,影响萘的动力学酸度。用有机金属或二烷基氨基锂型碱和二氧化碳连续处理 1-和 2-(三氟甲基)萘。由于单电子转移引发的副反应,(三氟甲基)萘甲酸的产率适中至差。正如预期的那样,1-(三氟甲基)萘仅在 2 位受到攻击。2-异构体在叔丁醇钾存在下仅在 1-位与叔丁基锂反应,但在 N,N,N',N'-四甲基乙二胺存在下与仲丁基锂同时在 3-和4个位置。制备了关键酸的正宗样品。基于独立、明确的方法。