| KONHEFR, Martin, Lenka MICHALCOVÁ, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL, Ctibor MAZAL and Karel LACINA. Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride. Tetrahedron Letters. Oxford: Pergamon-Elsevier Science Ltd, 2020, vol. 61, No 9, p. 1-4. ISSN 0040-4039. Available from: https://dx.doi.org/10.1016/j.tetlet.2019.151535. |
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@article{1620636,
author = {Konhefr, Martin and Michalcová, Lenka and Skrutková Langmajerová, Monika and Glatz, Zdeněk and Skládal, Petr and Mazal, Ctibor and Lacina, Karel},
article_location = {Oxford},
article_number = {9},
doi = {http://dx.doi.org/10.1016/j.tetlet.2019.151535},
keywords = {Ferrocene; Boronic acid; Electrochemically facilitated interaction; Alkali metal complexation; Imine bond},
language = {eng},
issn = {0040-4039},
journal = {Tetrahedron Letters},
title = {Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride},
url = {https://www.sciencedirect.com/science/article/pii/S0040403919313346},
volume = {61},
year = {2020}
}
TY - JOUR
ID - 1620636
AU - Konhefr, Martin - Michalcová, Lenka - Skrutková Langmajerová, Monika - Glatz, Zdeněk - Skládal, Petr - Mazal, Ctibor - Lacina, Karel
PY - 2020
TI - Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride
JF - Tetrahedron Letters
VL - 61
IS - 9
SP - 1-4
EP - 1-4
PB - Pergamon-Elsevier Science Ltd
SN - 00404039
KW - Ferrocene
KW - Boronic acid
KW - Electrochemically facilitated interaction
KW - Alkali metal complexation
KW - Imine bond
UR - https://www.sciencedirect.com/science/article/pii/S0040403919313346
L2 - https://www.sciencedirect.com/science/article/pii/S0040403919313346
N2 - 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.
ER -
KONHEFR, Martin, Lenka MICHALCOVÁ, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL, Ctibor MAZAL and Karel LACINA. Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride. \textit{Tetrahedron Letters}. Oxford: Pergamon-Elsevier Science Ltd, 2020, vol.~61, No~9, p.~1-4. ISSN~0040-4039. Available from: https://dx.doi.org/10.1016/j.tetlet.2019.151535.
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