Ring lithiation of 1,8-bis(dimethylamino)naphthalene: another side of the 'proton sponge coin'

被引：14

作者：

Antonov, Alexander S. ^{[1
]}

Pozharskii, Alexander F. ^{[1
]}

Ozeryanskii, Valery A. ^{[1
]}

Filarowski, Aleksander ^{[2
,3
]}

Suponitsky, Kyrill Yu. ^{[4
]}

Tolstoy, Peter M. ^{[5
]}

Vovk, Mikhail A. ^{[5
]}

机构：

[1] Southern Fed Univ, Dept Organ Chem, Rostov Na Donu 344090, Russia

[2] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland

[3] Joint Inst Nucl Res, Frank Lab Neutron Phys, Dubna 141980, Russia

[4] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

[5] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

来源：

DALTON TRANSACTIONS | 2015年 / 44卷 / 40期

基金：

俄罗斯基础研究基金会;

关键词：

PERI-NAPHTHYLENEDIAMINES; HYDROGEN-BOND; SPECTROSCOPY; CONFORMERS; BASE;

D O I：

10.1039/c5dt02482j

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

It has been found that 1,8- bis(dimethylamino) naphthalene (DMAN), unlike N,N-dimethylaniline, undergoes ring metallation in the n-BuLi-TMEDA-Et2O system with a low selectivity and in poor total yields. The situation is significantly improved in the t-BuLi- TMEDA-n-hexane system when 3- and 4-lithium derivatives become the only reaction products obtained in good yields. The formation of 3-Li-DMAN is especially desired since no method of direct meta-functionalization of DMAN is known to date. The relative stability and structure of DMAN lithium derivatives have been examined with the help of X-ray and multinuclear NMR measurements as well as DFT calculations.

引用

页码：17756 / 17766

页数：11

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