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Synthesis 2014; 46(23): 3273-3282
DOI: 10.1055/s-0034-1379008
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© Georg Thieme Verlag Stuttgart · New York

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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Publication History

Received: 25 June 2014

Accepted after revision: 31 July 2014

Publication Date:
26 August 2014 (online)

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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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