ortho-Ketimines of 1,8-Bis(dimethylamino)naphthalene: Synthesis, Hydrolytic Stability and Transfer of Basicity from Proton Sponge Moiety to the Imino Function

Alexander S. Antonov; Vladimir Y. Mikshiev; Alexander F. Pozharskii; Valery A. Ozeryanskii

doi:10.1055/s-0034-1379008

Synthesis, Table of Contents

Synthesis 2014; 46(23): 3273-3282
DOI: 10.1055/s-0034-1379008

paper

ortho-Ketimines of 1,8-Bis(dimethylamino)naphthalene: Synthesis, Hydrolytic Stability and Transfer of Basicity from Proton Sponge Moiety to the Imino Function

Alexander S. Antonov

Department of Organic Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation Fax: +7(863)2975146 Email: apozharskii@sfedu.ru

,

Vladimir Y. Mikshiev

Department of Organic Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation Fax: +7(863)2975146 Email: apozharskii@sfedu.ru

,

Alexander F. Pozharskii*

Department of Organic Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation Fax: +7(863)2975146 Email: apozharskii@sfedu.ru

,

Valery A. Ozeryanskii

Department of Organic Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation Fax: +7(863)2975146 Email: apozharskii@sfedu.ru

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Abstract

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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.

Key words

amines - imines - hydrolysis - ketones - organometallic reagents

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References

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