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Unexpected reactivity of ferrocenyl-iminoboronates: breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2019-12-18 , DOI: 10.1016/j.tetlet.2019.151535
Martin Konhefr , Lenka Michalcová , Monika Skrutková Langmajerová , Zdeněk Glatz , Petr Skládal , Ctibor Mazal , Karel Lacina

The boronic acid moiety in the proximity of electron-donating structures in ((ferrocenylimino)methyl)phenylboronic acid 1 significantly improves the reactivity of the molecule. The ortho regioisomer 1a exhibits a two-fold higher affinity to NaCl compared to its meta 1b and para 1c isomers, respectively. Moreover, the double imine bond in 1a was broken by the interaction with NaCl in methanol upon activation by electrochemical oxidation.



中文翻译:

二茂铁基-亚氨基硼酸酯的意外反应性:在非水氯化钠存在下,通过氧化作用破坏亚胺键

((二茂铁基亚氨基)甲基)苯基硼酸1中供电子结构附近的硼酸部分显着提高了分子的反应性。的邻位位置异构体1a中显示出2倍至NaCl的相比,其较高的亲和力的元 1B 1C分别异构体,。此外,通过电化学氧化活化后,与甲醇中的NaCl相互作用会破坏1a中的双亚胺键。

更新日期:2019-12-19
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