Ortho-ketimines of 1,8-bis(dimethylamino)naphthalene: Synthesis, hydrolytic stability and transfer of basicity from proton sponge moiety to the imino function
Aug 26, 2014·
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Dr. Alexander Antonov
Dr. Vladimir Mikshiev
Prof. Alexander Pozharskii
V. A. Ozeryanskii
Corresponding author
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Abstract
A series of 2-ketimines and 2,7-diketimines of 1,8-bis(dimethylamino)naphthalene (proton sponge, DMAN) have been obtained and converted into the corresponding ketones via acidic hydrolysis. Investigation of structural and spectral properties of DMAN-based imines led to the conclusion that their unusual hydrolytic stability results from a combination of different factors the most important of which is a strong electron-donor effect of peri-dimethylamino groups.
Publication
Synthesis 2014, 46, 3273–3282
Authors
1938-2025
Prof. Pozharskii was not only my PhD supervisor, but he was a beacon in the scientific world for me. He taught me how to properly plan an experiment, how to write research papers, how to supervise students, how to make grant applications, and how to give lectures. I am who I am today thanks to Prof. Pozharskii and his contribution to me.
Authors