Study of the Reactivities of Acid-Catalyzed O-Benzylating Reagents Based on Structural Isomers of 1,3,5-Triazine
Study of the Reactivities of Acid-Catalyzed O-Benzylating Reagents Based on Structural Isomers of 1,3,5-Triazine
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DOI：
10.1021/acs.joc.5b02059
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发表时间：
2015-11-06
影响因子：
3.6
通讯作者：
Kunishima, Munetaka
中科院分区：
文献类型：
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作者：
Fujita, Hikaru;Hayakawa, Naoko;Kunishima, Munetaka
我们已经证明了 4,6-bis(benzyloxy)-1,3,5-triazin-2(1H)-one (DiBOT) 和 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (MonoBOT) 的 O-苄基化能力，之前已建议将其作为酸催化苄基化的反应中间体2,4,6-三(苄氧基)-1,3,5-三嗪(TriBOT)。我们通过进行动力学研究并使用模型化合物估计相对碱度，研究了这些化合物中异构核心三嗪结构对酸催化 O-苄基化反应活性的影响。由于 MonoBOT 显示出优异的反应活性，1,3,5-三嗪-2,4(1H,3H)-二酮是酸催化烷基化试剂的有前途的核心结构。
We have demonstrated O-benzylating abilities of both 4,6-bis(benzyloxy)-1,3,5-triazin-2(1H)-one (DiBOT) and 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (MonoBOT), which have been previously suggested as reaction intermediates of the acid-catalyzed benzylation of 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT). We studied the effect on the reactivity of acid-catalyzed O-benzylation caused by the isomeric core triazine structures in these compounds by carrying out a kinetic study and estimating relative basicities using model compounds. Since MonoBOT showed superior reactivity, 1,3,5-triazine-2,4(1H,3H)-dione is a promising core structure for acid-catalyzed alkylating reagents.