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：

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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。