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, Inhaltsverzeichnis

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

Autoren

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

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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Referenzen

References

1a Layer RW. Chem. Rev. 1963; 63: 489
1b Clayden J, Greeves N, Warren S, Wothers P. Organic Chemistry . Oxford University Press; Oxford: 2001: 349-354
1c Nelson DL, Cox MM. Lehninger Principles of Biochemistry . 4th ed. Worth; New York: 2004

2 Povalyakhina MA, Antonov AS, Dyablo OV, Ozeryanskii VA, Pozharskii AF. J. Org. Chem. 2011; 76: 7157
3 Pozharskii AF, Degtyarev AV, Ryabtsova OV, Ozeryanskii VA, Kletskii ME, Starikova ZA, Sobczyk L, Filarowski A. J. Org. Chem. 2007; 72: 3006
4 Pozharskii AF, Ozeryanskii VA. Proton Sponges . In The Chemistry of Anilines . Part 2; Rappoport Z. Wiley; Chichester: 2007: 931-1026
5 Pozharskii AF, Degtyarev AV, Ozeryanskii VA, Ryabtsova OV, Starikova ZA, Borodkin GS. J. Org. Chem. 2010; 75: 4706

6a Yao C.-F, Chen Y.-S, Chen W.-C, Sheu R.-S, Laj J.-K, Ueng C.-H. Acta. Crystallogr., Sect. C 1997; 53: 956
6b Zimmerman HE, Wright CW. J. Am. Chem. Soc. 1992; 114: 6603
6c Scepaniak JJ, Wu G, Hayton TW. Dalton Trans. 2012; 41; 7859
6d Biehl ER, Dutt M, Fravel B, Zhang H. J. Chem. Soc., Chem. Commun. 1992; 1520

7 Boiko LZ, Sorokin VI, Filatova EA, Starikova ZA, Ozeryanskii VA, Pozharskii AF. J. Mol. Struct. 2011; 1005: 12
8 Albert A, Serjeant E. Ionization Constants of Acids and Bases . Wiley; New York: 1962
9 Effenberger F. Acc. Chem. Res. 1989; 22: 27
10 Ozeryanskii VA, Pozharskii AF, Filarowski A, Borodkin GS. Org. Lett. 2013; 15: 2194
11 Kögel JF, Xie X, Baal E, Gesevičius D, Oelkers B, Kovačevic B, Sundermeyer J. Chem. Eur. J. 2014; 20: 7670
12 Ozeryanskii VA, Pozharskii AF, Antonov AS, Filarowski A. Org. Biomol. Chem. 2014; 12: 2360

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