Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride
| Autor: | Martin Konhefr, Zdeněk Glatz, Monika Skrutková Langmajerová, Ctibor Mazal, Petr Skládal, Lenka Michalcová, Karel Lacina |
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| Rok vydání: | 2020 |
| Předmět: |
Aqueous solution
010405 organic chemistry Chemistry Organic Chemistry Imine 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Ferrocene Drug Discovery Moiety Molecule Reactivity (chemistry) Phenylboronic acid Boronic acid |
| Zdroj: | Tetrahedron Letters. 61:151535 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2019.151535 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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